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[ CAS No. 59878-57-8 ] {[proInfo.proName]}

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Chemical Structure| 59878-57-8
Chemical Structure| 59878-57-8
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Product Details of [ 59878-57-8 ]

CAS No. :59878-57-8 MDL No. :MFCD06369645
Formula : C8H14N2O Boiling Point : -
Linear Structure Formula :- InChI Key :KIALFUYSJAAJSU-UHFFFAOYSA-N
M.W : 154.21 Pubchem ID :2064235
Synonyms :

Calculated chemistry of [ 59878-57-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.88
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.07
TPSA : 32.34 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.79
Log Po/w (XLOGP3) : -0.48
Log Po/w (WLOGP) : -1.0
Log Po/w (MLOGP) : 0.28
Log Po/w (SILICOS-IT) : 0.91
Consensus Log Po/w : 0.3

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.36
Solubility : 67.1 mg/ml ; 0.435 mol/l
Class : Very soluble
Log S (Ali) : 0.27
Solubility : 286.0 mg/ml ; 1.85 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.91
Solubility : 19.0 mg/ml ; 0.123 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.25

Safety of [ 59878-57-8 ]

Signal Word:Danger Class:9
Precautionary Statements:P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501 UN#:3082
Hazard Statements:H302-H317-H318-H410 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 59878-57-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 59878-57-8 ]

[ 59878-57-8 ] Synthesis Path-Downstream   1~12

  • 2
  • [ 955027-61-9 ]
  • [ 59878-57-8 ]
  • 4-[3-(4-cyclopropanecarbonyl-piperazin-1-yl)-propyl]-1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; borane pyridine; acetic acid; In ethanol; 1,2-dichloro-ethane; Examples 35-92; General Procedure for Examples 35-92; A solution of 3-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-propionaldehyde (intermediate 2) (0.037 g, 0.1 mmol) in DCE (0.5 ml) was added to the appropriate amine (0.1 mmol) followed by a freshly prepared solution of pyridine-borane complex (25 ul, 8M in pyridine, 0.2 mmol) and acetic acid (25 ul) in EtOH (0.5 ml). The reaction was then shaken overnight, concentrated and the residue purified by preparative HPLC.
  • 3
  • [ 59878-57-8 ]
  • [ 57184-25-5 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride; In tetrahydrofuran; for 0.5h;Heating / reflux; Lithium aluminium hydride (770 mg, 20.3 mmol) was suspended in tetrahydrofuran (150 mL), <strong>[59878-57-8]1-(cyclopropylcarbonyl)piperazine</strong> (1.56 g, 10.1 mmol) was gradually added thereto, and the reaction mixture was heated under reflux for 30 minutes. The reaction mixture was cooled to room temperature, and 0.8 mL of water, 0.8 mL of a 15% aqueous solution of sodium hydroxide and 2.3 mL of water were sequentially gradually added thereto. The precipitated insoluble matter was removed by filtration through Celite, and the filtrate was evaporated to give the title compound (1.40g) as a colorless oil. The product was used for the synthesis of (8E,12E,14E)-7-((4-cyclopropylmethylpiperazin-1-yl)carbonyl)oxy-3,6,16,21-tetrahydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (the compound of Example 27) without further purification.1H-NMR Spectrum (CDCl3,400MHz) delta(ppm): 0.09-0.15(2H,m), 0.48-0.56(2H,m),0.82-0.93(1H,m),2.25(2H,d,J=7.2Hz) 2.48-2.65(4H,m),2.90-2.99(4H,m).
  • 4
  • [ 629625-92-9 ]
  • [ 59878-57-8 ]
YieldReaction ConditionsOperation in experiment
97.3% With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; In 100 mL of ethanol was dissolved benzyl 4-(cyclopropylcarbonyl)piperazine-1-carboxylate (3.00 g,10.4 mmol), and 1.5 g of 10% palladium-carbon was added thereto, followed by stirring at room temperature under hydrogen atmosphere overnight. The palladium-carbon was removed by filtration, and the filtrate was evaporated to give the title compound (1.50 g, 97.3%) as a colorless oil.1H-NMR Spectrum (CDCl3,400MHz) delta(ppm): 0.73-0.80(2H,m), 0.96-1.03(2H,m),1.67-1.77(1H,m),2.82-2.97(4H,m),3.60-3.71 (4H,m).
  • 5
  • [ 414910-03-5 ]
  • [ 59878-57-8 ]
  • 4-(R)-(4-cyclopropanoyl-piperazin-1-yl)-2-(R)-(4-fluoro-2-methyl-phenyl)-piperidine-1-carboxylic acid [1-(R)-(3,5-bis-trifluoromethyl-phenyl)-ethyl]-methylamide [ No CAS ]
  • 4-(S)-(4-cyclopropanoyl-piperazin-1-yl)-2-(R)-(4-fluoro-2-methyl-phenyl)-piperidine-1-carboxylic acid [1-(R)-(3,5-bis-trifluoromethyl-phenyl)-ethyl]-methylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
A solution of intermediate 4a (100 mg) and intermediate 12 (31 mg) in dry 1,2-dichloroethane (5 mL) and acetonitrile (1 mL) was stirred at r.t. for 30 minutes under a nitrogen atmosphere. Then, sodium triacetoxyborohydride (42 mg) was added and the mixture was stirred at 23 C. for 24 hours. The solution was diluted with AcOEt and washed with water. The organic layer was dried and concentrated in vacuo to a residue which was purified by flash chromatography (AcOEt/MeOH 9:1) to give: [0379] example 11a (2 mg-T.I.c.: AcOEt/MeOH 8:2 Rf=0.33), [0380] example 11b (7 mg-T.I.c.: AcOEt/MeOH 8:2 Rf=0.16).
  • 6
  • [ 414910-15-9 ]
  • [ 59878-57-8 ]
YieldReaction ConditionsOperation in experiment
97% With trifluoroacetic acid; In dichloromethane; at 20 - 30℃;Inert atmosphere; 1-Tertbutoxycarbonyl-4-(cyclopropanecarbonyl) piperazine (190 mg, 0.75 mmol) was dissolved in dichloromethane, and then trifluoroacetic acid (1 mL) was added. The reaction mixture was stirred at room temperature until complete reaction, and then washed with saturated sodium bicarbonate solution for three times. The organic phases were concentrated to give 112 mg (yield 97%) pale yellow solid of N-(cyclopropanecarbonyl) piperazine for use.
97% With trifluoroacetic acid; In dichloromethane; at 20℃; 1 -Tertbutoxycarbonyl-4-(cyclopropanecarbonyl)piperazine (190 mg, 0.75 mmol) was dissolved in dichloromethane, and then trifluoroacetic acid (1 mE) was added. The reaction mixture was stirred at room temperature until complete reaction, and then washed with saturated sodium bicarbonate solution for three times. The organic phases were concentrated to give 112mg (yield 97%) pale yellow solid of N-(cyclopropanecarbonyl) piperazine for use.
With trifluoroacetic acid; In dichloromethane; at 20℃; for 2h; TFA (965 muL) was added to a solution of intermediate 11 (210 mg) in anhydrous DCM (1 mL). The solution was stirred at r.t. for 2 hours, then it was concentrated in vacuo. The residue was diluted in a saturated potassium carbonate solution (10 mL) and extracted with AcOEt (2×20 mL). The combined organic extracts were dried and concentrated in vacuo to give the title compound (110 mg) as an oil. [0244] T.I.c.: AcOEt, Rf=0.14. [0245] IR (CDCl3, cm-1): 1626 (CO). [0246] NMR (CDCl3): delta (ppm) 3.7 (bs, 1H); 3.63 (bd, 4H); 2.88 (bd, 4H); 1.72 (m, 1H); 0.99 (m, 2H); 0.75 (m, 2H). [0247] MS (ES/+): m/z=155 [M+H]+.
  • 7
  • [ 13623-25-1 ]
  • [ 59878-57-8 ]
  • 1-(Cyclopropylcarbonyl)-4-(6-methoxy-indan-1-yl)piperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; sodium borohydrid;titanium(IV) isopropylate; In ethanol; Example 15 1-Cyclopropylcarbonyl-4-(6-methoxy-indan-1-yl)piperazine An intimate mixture of 6-methoxy-1-indanone (1.6 g, 10 mmol), 1-cyclopropanecarbonylpiperazine (1.5 g, 10 mmol) and titanium(IV) isopropoxide (4 mL, 12 mmol) was heated on the steam bath for 10 minutes. Additional titanium isopropoxide (1 mL, 3 mmol) was added and the mixture stirred for 20 hr. The material was dissolved in ethanol and sodium borohydride added (0.9 g, 22 mmol). After stirring for 1 hr the solution was heated to reflux and more sodium borohydride (0.9 g, 22 mmol) added. When solution had occurred 15% NaOH solution (50 mL) was added. The insoluble material was removed and discarded. The solution was concentrated in vacuo and the residue mixed with ether. The mixture was washed with water and 1N HCl solution. The acid washes were made basic and the mixture was extracted with ether to give the product as an oil which was converted to the fumarate salt and crystallized from acetone to give the salt (1.8 g).
  • 8
  • [ 23680-84-4 ]
  • [ 59878-57-8 ]
  • [ 64579-61-9 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 2 4-Amino-2-[4-(cyclopropylcarbonyl)-1-piperazinyl]-6,7-dimethoxyquinazoline <strong>[59878-57-8]N-(Cyclopropylcarbonyl)piperazine</strong> (3.08 g., 0.02 mole) and 2-chloro-4-amino-6,7-dimethoxyquinazoline (4.74 g., 0.02 mole) are reacted according to the procedure of Example 1(a). The crude product crystallized from ethanol affords analytically pure 4-amino-2-[4-(cyclopropylcarbonyl)-1-piperazinyl]-6,7-dimethoxyquinazoline, m.p. 283.5-285.5 C. (corr.). Analysis. Calcd. for C18 H23 N5 O3 (percent): C, 60.49; H, 6.49; N, 19.59. Found (percent): C, 60.56; H, 6.46; N, 19.41.
Example 128 4-Amino-2-[4-(cyclopropylcarbonyl)-1-piperazinyl]-6,7-dimethoxyquinazoline <strong>[59878-57-8]N-(Cyclopropylcarbonyl)piperazine</strong> (3.08 g., 0.02 mole) and 2-chloro-4-amino-6,7-dimethoxyquinazoline (4.74 g., 0.02 mole) are reacted according to the procedure of Example 127(a). The crude product crystallized from ethanol affords analytically pure 4-amino-2-[4-(cyclopropylcarbonyl)-1-piperazinyl]-6,7-dimethoxyquinazoline, m.p. 283.5 C. (corr.). Analysis, Calcd. for C18H23N5O3 (percent): C, 60.49; H, 6.49; N, 19.59. Found (percent): C, 60.56; H, 6.46; N, 19.41.
  • 9
  • [ 362474-71-3 ]
  • [ 59878-57-8 ]
YieldReaction ConditionsOperation in experiment
97% With hydrogen;palladium 10% on activated carbon; In ethanol; under 760.051 Torr; 10% Palladium on carbon (175 mg, 10% by wt.) was placed under an inert atmosphere and suspended in EtOH (5 mL). A solution of (4-benzyl-piperazin-1-yl)-cyclopropyl- methanone (1.75 g, 7.16 mmol) dissolved in EtOH (25 mL) was added. The reaction mixture was placed under H2 atmosphere (1 atmosphere pressure) and stirred overnight.The resulting mixture was filtered through a pad of Celite and the solvent was concentrated in vacuo to give 1.07 g (97%) of the title compound as a clear oil. 1H-NMR(300 MHz, CD3OD) delta 3.74 (broad s, 2H), 3.57 (broad s, 2H), 2.87 (broad s, 2H), 2.80 (broad s, 2H), 1.97 to 1.91 (m, 1 H), 0.89 to 0.78 (m, 4H); ES-MS m/z 154.9 [M+H]+, RT(min) 1.02.
  • 10
  • [ 763114-26-7 ]
  • [ 59878-57-8 ]
  • olaparib [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% To the reaction flask was added compound 6 (prepared in Example 3-2, 256.5g,0.86mol), CDI (139.45g, 0.86mol), 1.6LTHF, after stirring for 0.5h Compound 7 (138.8g,0.90mol) at room temperature The reaction 3h, after completion of the reaction, water was added to quench the reaction, of THF was distilled off under reduced pressure, theresidue was dissolved in ethyl acetate was added, the organic phase was separated,washed with water three times, the organic phase was dried over anhydrous Na 2SO 4Dried,filtered and concentrated to give Ola Trapani (356.3g, 0.82mol), yield 95%, HPLC purity 99.8%.
91.5% With pivaloyl chloride; triethylamine; In ethanol; dichloromethane; at 20℃; for 4h; (4) The product of the previous step (0.3 g, 1 mmol) was weighed, dissolved in 5 mL of dichloromethane, and trimethylacetyl chloride (121 yL, 1 mmol) and triethylamine (208 mL, 1.5 mmol) were stirred at room temperature. The reaction was clarified until the solution was clarified. 1 - (cyclopropylcarbonyl)-pyridazine (0.3 g, 2 mmol) was dissolved in 5 mL of ethanol, added dropwise to the above clear solution, reacted at room temperature for 4 h, and extracted with dichloromethane (15 mL). The organic phase was washed with water, and the organic layer was dried over anhydrous sodium sulfate, and then evaporated to dryness to afford ololani (0.4 g, 0.9 mmol), yield 91.5%, purity 99.8%.
81.9% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 30 - 50℃; In a 500 mL reaction flask, 2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid (Formula II, 15.0 g, 50.3 mmol) and DMF ( 100ml),After the addition, the system was stirred for 0.5 h to dissolve the system, and then 1-cyclopropyl-formylpiperazine (8.55 g, 55.4 mmol) and HBTU (21.0 g, 55.4 mmol) were added.DIPEA (8.5 g, 65.8 mmol) was then added dropwise to the system.The dropping process controls the reaction temperature not to be higher than 50 C, and the system is kept at 30 ± 5 C overnight after the addition.After the reaction was completed, the mixture was filtered, and the filter cake was washed with 1 L of purified water, and then the filter cake was transferred to a 1 L reaction flask.Purified water (500 mL) was added, kept at 30 ± 5 C, and stirred for 1 h.After suction filtration, the filter cake was washed with purified water (100 mL) and blast dried for about 24 h.The crude product (19.7 g) was obtained, and the crude material was recrystallized from DMF (75 ml)17.9g, 81.9%).
34% To a solution of 2-Fluoro-5-((4-oxo3,4-dihydrophthalazin-l-yl)methyl)benzoic acid (50 mg, 0.168 mmol) in DMA (1 mL) was added DIPEA (56 L, 0.336 mmol) and HBTU (64 mg, 0.170 mmol). The reaction mixture was stirred for 1 hour before addition of cyclopropylpiperazine-l-ylmethanone (0.170 mmol) was carried out. The reaction mixture was stirred at room temperature for 48 h. The reaction mixture was then extracted with DCM (3 x 5 mL) and washed with water (3 x 20 mL). The organic layers were collected, dried with MgS04 and the excess solvent removed in vacuo. Purification via reverse phase HLPC was carried out affording 4-(3-(4 (cyclopropanecarbonyl) piperazine- l-carbonyl)-4- fluorobenzy phthalazin- 1 (2//)-one (olaparib) (25 mg, 34%) as a white solid. *H NMR (400 MHz, CDCh) d = 10.65 (s, 1H), 8.44 - 8.37 (m, 1H), 7.75 - 7.61 (m, 3H), 7.34 - 7.22 (m, 2H), 6.97 (t, J = 8.9 Hz, 1H), 4.22 (s, 2H), 3.90 - 3.09 (m, 8H), 1.79 - 1.52 (s, 3H), 0.99 - 0.88 (m, 2H), 0.81 - 0.63 (s, 2H); {}1^ NMR (376 MHz, CDCb) d = - 117.6; Mp: 69 - 7lC. Data is in accordance with known literature (Menear, K.A., et al., ibid.).
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 3 - 20℃; for 3.5h;Product distribution / selectivity; Example 2: Alternative synthesis of Compound A using i-fcyclopropylcarbonyl) piperazineMethods (also for Examples 3 & 4)NMR1H NMR spectra were recorded using Bruker DPX 400 spectrometer at 400 MHz. Chemical shifts were reported in parts per million (ppm) on the delta scale relative to tetramethylsilane internal standard. Unless stated otherwise all samples were dissolved in DMSOd6.Mass SpectraMass spectra were recorded on an Agilent XCT ion trap mass spectrometer using tandem mass spectrometry (MS/MS) for structural confirmation. The instrument was operated in a positive ion elctrospray mode.(a) 4-[3-(4-Cyclopropanecarbonyl-piperazine-1-carbonyl)-4-fluoro-benzyl]-2H-phthalazin-1-one (Compound A)2-Fluoro-5-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzoic acid (D)(15.23g, 51.07 mmol) was suspended with stirring under nitrogen in acetonitrile (96 ml). Diisopropylethylamine (19.6 ml, 112.3 mmol) was added followed by 1-cyclopropylcarbonylpiperazine (l)(9.45g, 61.28 mmol) and acetonitrile (1 ml). The reaction mixture was cooled to 18C. O-Benzotriazol-1-yl- tetramethyluronium hexafluorophosphate (25.18g, 66.39 mmol) was added over 30 minutes and the reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was cooled to 3C and maintained at this temperature for 1 hour, before being filtered. The filter cake was washed with cold (3C) acetonitrile (20 ml) before being dried in vacuo at up to 4O0C to give the title compound as a pale yellow solid (20.21 g).Mass Spectrum: MH+ 4351H NMR (400MHz. DMSO-d6) delta: 0.70 (m, 4H), 1.88 (br s, 1 H), 3.20 (br s, 2H), 3.56 (m, 6H), 4.31 (s, 2H), 7.17 (t, 1 H), 7.34 (dd, 1 H), 7.41 (m, 1 H), 7.77 (dt, 1 H), 7.83 (dt, 1 H), 7.92 (d, 1 H), 8.25 (dd, 1 H), 12.53 (s, 1 H).
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 3 - 20℃; for 3.5h; (a) 4-[3-(4-Cyclopropanecarbonyl-piperazine-1-carbonyl)-4-fluoro-benzyl]-2H-phthalazin-1-one (Compound A)2-Fluoro-5-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzoic acid (D)(15.23g, 51.07 mmol) was suspended with stirring under nitrogen in acetonitrile (96 ml). Diisopropylethylamine (19.6 ml, 112.3 mmol) was added followed by 1-cyclopropylcarbonylpiperazine (l)(9.45g, 61.28 mmol) and acetonitrile (1ml). The reaction mixture was cooled to 18C. O-Benzotriazol-1-yl- tetramethyluronium hexafluorophosphate (25.18g, 66.39 mmol) was added over 30 minutes and the reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was cooled to 3C and maintained at this temperature for 1 hour, before being filtered. The filter cake was washed with cold (3C) acetonitrile (20 ml) before being dried in vacuo at up to 400C to give the title compound as a pale yellow solid (20.21 g).Mass Spectrum: MH+ 4351H NMR (400MHz, DMSO-d6) delta: 0.70 (m, 4H), 1.88 (br s, 1H), 3.20 (br s, 2H), 3.56 (m, 6H), 4.31 (s, 2H), 7.17 (t, 1H), 7.34 (dd, 1 H), 7.41 (m, 1H), 7.77 (dt, 1H), 7.83 (dt, 1H), 7.92 (d, 1H), 8.25 (dd, 1 H)1 12.53 (S1 1H).

  • 11
  • [ 1036392-29-6 ]
  • [ 59878-57-8 ]
  • [ 1073659-91-2 ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In ISOPROPYLAMIDE; at 20℃; for 18h; (e) Library Synthesis (10a-m)To a solution of 2-fluoro-5-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-benzoic acid (22 mg, 0.07 mmol), in DMA (1 ml) was added HBTU (53 mg, 0.140 mmol), triethylamine (20 muL, 0.140 mol) and amine (0.140 mmol). The crude reaction mixture was stirred for 18 hours at room temperature and then submitted for preparative HPLC purification.
  • 12
  • [ 1036393-27-7 ]
  • [ 59878-57-8 ]
  • C24H28N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In dichloromethane; at 20℃; for 18h; (d) Library Synthesis (5a-h)To a solution of 3-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-benzoic acid (4) (20 mg, 0.07 mmol), in DCM (1 ml) was added HBTU (53 mg, 0.140 mmol), triethylamine (20 muL, 0.140 mol) and amine (0.140 mmol). The reaction mixture was stirred for 18 hours at room temperature and concentrated in vacuo. The crude samples were submitted for preparative HPLC purification.
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