[ CAS No. 876-08-4 ] {[proInfo.proName]}

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Quality Control of [ 876-08-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 876-08-4 ]

SDS Specification

Alternatived Products of [ 876-08-4 ]

Product Details of [ 876-08-4 ]

CAS No. :	876-08-4	MDL No. :	MFCD00053224
Formula :	C₈H₆Cl₂O	Boiling Point :	-
Linear Structure Formula :	ClCH₂C₆H₄C(O)Cl	InChI Key :	RCOVTJVRTZGSBP-UHFFFAOYSA-N
M.W :	189.04	Pubchem ID :	70136
Synonyms :

Calculated chemistry of [ 876-08-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.39
TPSA :	17.07 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.03
Log Po/w (XLOGP3) :	3.1
Log Po/w (WLOGP) :	2.65
Log Po/w (MLOGP) :	2.67
Log Po/w (SILICOS-IT) :	3.3
Consensus Log Po/w :	2.75

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.24
Solubility :	0.11 mg/ml ; 0.00058 mol/l
Class :	Soluble
Log S (Ali) :	-3.13
Solubility :	0.141 mg/ml ; 0.000747 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.98
Solubility :	0.0196 mg/ml ; 0.000104 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.02

Safety of [ 876-08-4 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P261-P280-P305+P351+P338-P310	UN#:	3261
Hazard Statements:	H314-H335	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 876-08-4 ]

* 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 [ 876-08-4 ]

[ 876-08-4 ] Synthesis Path-Downstream 1~12

1
[ 110-85-0 ]
[ 876-08-4 ]
[ 107819-90-9 ]
MeO-poly(ethylene glycol) [ No CAS ]
[ 220213-06-9 ]

Reference： [1]Synlett,1998,p. 1423 - 1425

2
[ 505-66-8 ]
[ 876-08-4 ]
[ 107819-90-9 ]
MeO-poly(ethylene glycol) [ No CAS ]
[ 220213-07-0 ]

Reference： [1]Synlett,1998,p. 1423 - 1425

3
[ 876-08-4 ]
[ 7144-05-0 ]
[ 107819-90-9 ]
MeO-poly(ethylene glycol) [ No CAS ]
[ 220213-05-8 ]

Reference： [1]Synlett,1998,p. 1423 - 1425

4
[ 876-08-4 ]
[ 152460-10-1 ]
[ 404844-11-7 ]

Yield	Reaction Conditions	Operation in experiment
97.4%	With triethylamine; In tetrahydrofuran; at 0℃; for 4h;	Example 15 Preparation of 4-((4-((5Z,8Z,llZ,14Z,17Z)-icosa-5,8,ll,14,17-pentaenoyl)piperazin-l- yl)methyl)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide (IV-5): [0311 ] The commercially available 6-methyl-N 1 -(4-(pyridin-3 -yl)pyrimidin-2- yl)benzene-l,3-diamine (10.0 g, 36.0 mmol) and Et3N (10.0 ml, 72.2 mmol) were taken up in THF (100 mL). The resulting solution was cooled to 0 C with stirring and maintained for 10 min. A solution of 4-(chloromethyl)benzoyl chloride (7.8 g, 41.4 mmol) in THF (50 mL) was added dropwise. After stirring at 0 C for four hours, water (500 ml) was added dropwise to the reaction mixture, and a light-yellow precipitate appeared. The resulting precipitate was collected by suction filtration, washed with water ( 2 x 500 ml), and dried under reduced pressure to afford 4-(chloromethyl)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2- yl)amino)phenyl)benzamide (15.1 g, yield: 97.4 %) as a light-yellow solid. This material (4 g, 93 mmol) and tert - butyl piperazinecarboxylate (8.8 g, 465 mmol) were dissolved in N- methyl-2-pyrrolidone (20 mL). The solution was reacted under microwave conditions at 120 C for 1 h. After cooling to room temperature, CH2CI2 (50 mL) was added to the reaction mixture. The resulting mixture was extracted with 1M HC1 (20 mL). The acidic aqueous phase was neutralized with sodium carbonate, and then extracted with CH2CI2 (2 x 50 mL). The combined organic layers were dried over anhydrous Na2S04, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography (pentane/EtOAc) to give 4 g of tert-butyl 4-(4-((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2- yl)amino)phenyl)carbamoyl)benzyl)piperazine-l-carboxylate (72% yield) as a yellow solid. This material (580 mg, 1 mmol) was dissolved in a solution of HC1 in EtOAc (5 mL, 4 M). The resulting reaction mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure to afford the HC1 salt of N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin- 2-yl)amino)phenyl)-4-(piperazin-l-ylmethyl)benzamide.MS (EI) calculated for C28H29N7O: 479.58; Found: 480 [M+H]+(5Z,8Z,l lZ,14Z,17Z)-Eicosa-5,8,l l,14,17-pentaenoic acid (EPA, 0.27 g, 0.92 mmol) was taken up in 15 mL of CH2C12 along with HATU (0.47 g, 1.24 mmol), Et3N (0.25 g, 2.49 mmol) and the HC1 salt of N-(4-methyl-3-((4-(pyridin-3- yl)pyrimidin-2-yl)amino)phenyl)-4-(piperazin-l-ylmethyl)benzamide (0.4 g, 0.83 mmol). The resulting reaction mixture was stirred at room temperature for 16 h. The reaction mixture was then diluted with CH2CI2 (100 mL). The organic layer was washed with aq.NH4Cl (3 x 100 mL), brine (3 x 100 mL), dried over anhydrous Na2S04 and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (Gradient elution, 2: 1 pentane/EtOAc to 100% EtOAc) to afford 0.4 g of 4-((4-((5Z,8Z,l lZ,14Z,17Z)-icosa- 5,8,11,14,17-pentaenoyl)piperazin- 1 -yl)methyl)-N-(4-methyl-3 -((4-(pyridin-3 -yl)pyrimidin- 2-yl)amino)phenyl)benzamide (62% yield). MS (EI) calculated for C48H57N702: 764.01; Found: 765.05 [M+H] +
95 - 98%	With potassium carbonate; In tetrahydrofuran; at 0 - 20℃; for 1.16667 - 4.25h;Conversion of starting material;	Example 6 4-Methyl-N-3-(4-pyridin-3-ylpyrimidin-2-yl)-benzene- 1,3- diamine (18.488 g, 0.067 M) was dissolved in THF (255 mL), freshly EPO <DP n="27"/>ground potassium carbonate (19.870 g, 0.143 M) was added and then the mixture was cooled down to 0C. A solution of 4- chloromethylbenzoyl chloride (13.863 g, 0.073 M) in THF (69 niL) was added dropwise within 15 minutes while temperature of the reaction mixture was maintained at 00C. The reaction mixture was stirred at this temperature for 2 hours and for another 2 hours at room temperature. Water was added dropwise at a very low rate. Temperature of the reaction has risen to 26C. At this temperature dropwise addition of water was continued with cooling. Cooling was discontinued when temperature dropped below 19C. When water addition was completed (in total 543 mL), temperature of the reaction mixture was 26C. The reaction mixture was stirred for further 30 min. A solid precipitate was filtered off and washed with water (150 mL) to afford 28.06 g (yield 97%) of the title compound in the form of a colourless crystalline solid.M.p. 211-212C. 1H NMR (DMSO-dbeta): 10.24 (IH, s), 9.28 (IH, d, J=l,8), 8.99 (IH, s), 8.69 (IH, dd, J=4.8-1.4), 8.52 (IH, d, J=5,2), 8.48 (IH, dt, J=8.2-1.8), 8.09 (IH, d, J=2.0), 7.96 (2H, d, J=8.0), 7.51 (5H, m), 7.22 (IH, d, J=8.4), 4.85 (2H, s), 2.23 (3H, s). Example 7 4-Methyl-N-3-[(4-pyridin-3-yl)pyrimidin-2-yl]-benzene- 1,3- diamine (18.488 g, 0.067 M) was dissolved in THF (255 mL), freshly ground potassium carbonate (19.870 g, 0.143 M) was added and then the mixture was cooled down to 0C. A solution of 4- chloromethylbenzoyl chloride (13.863 g, 0.073 M) in THF (69 mL) was added dropwise within 10 minutes while temperature of the reaction mixture was maintained at approximately 200C. The reaction mixture was stirred at room temperature for 1 hour. Water was added dropwise (in total 543 mL) while maintaining temperature EPO <DP n="28"/>of the reaction mixture at approximately 200C, and then the reaction mixture was stirred for 80 min. A solid precipitate was filtered off and washed with water (150 mL) to afford 28.37 g (yield 98%) of the title compound. Example 8 4-Methyl-N-3-[(4-pyridin-3-yl)pyrimidin-2-yl]-benzene- 1 ,3- diamine (9.244 g, 33.3 niM) was dissolved in THF (128 mL), then a solution of potassium carbonate (9.935 g, 71.9 mM) in water (13 mL) was poured in. The mixture was cooled down to 0C and a solution of 4-chloromethylbenzoyl chloride (6.932 g, 36.7 mM) in THF (30 mL) was added dropwise within 15 minutes. The reaction mixture was stirred at 00C for 2 hours. Water (260 mL) was added dropwise with stirring and cooling the reaction flask and then at room temperature for further 30 min. A solid precipitate was filtered off and washed with water (120 mL) to afford 13.62 g (yield 95%) of the title compound.
94%	With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 7h;	4-(Chloromethyl)benzoylchloride (0.41 g, 2.16 mmol) wasslowly added to the mixture of compound 3(0.50g, 1.8 mmol) andEt3N(0.36 g, 3.6 mmol) in20 mL THF at 0 oC for 1 h. The resulting mixturewas stirred atroom temperature for 6 h. After the addition ofH2O,solid was formed and washed with water 5times to give theproduct with 94% yield (0.73 g, 1.69 mmol). 1H NMR (300 MHz, DMSO)delta 10.24 (s, 1H), 9.28(d, J = 1.5 Hz,1H), 8.98 (s, 1H), 8.68 (dd, J = 3.3 Hz, 1H), 8.52-8.46 (m, 2H), 8.10(d, J = 2.1 Hz, 1H), 7.96( d, J = 8.1 Hz, 2H), 7.60-7.40 (m, 5H), 7.21(d, J = 8.1 Hz, 1H), 4.84 (s, 2H), 2.23(s, 3H). 13CNMR (75 MHz, DMSO): delta164.9, 161.6, 161.1, 159.4, 151.4, 148.2, 140.1, 137.8, 137.1, 134.9, 134.4,132.2, 130.0, 128.7, 128.0, 127.7, 123.8, 117.2, 116.7, 107.5, 45.4, 17.7. HRMS(ESI) calcd. for C24H21ClN5O [M+H]+430.1435, found430.1433.

94.2%		_6-Methyl-N-(4-(pyridine-3-yl) pyrimidin-2-yl) benzene-1,3-diamine (1.24 g, 4.46 mmol) and TEA (1.4 mL, 8.92 mmol) was dissolved in THF (15 mL). The resulting solution was cooled to 0 C. with stirring and maintained for 10 minutes. A solution of 4-(chloromethyl)benzoyl chloride (0.97 g, 5.14 mmol) in THF (5 mL) was added dropwise. After stirring at 0 C. for 4 hours, water (140 mL) was added dropwise to the reaction mixture, and a light-yellow precipitate appeared. The resulting precipitate was collected by suction filtration, washed with water (300 mL), and dried under vacuum. The crude product was purified by column chromatography (biotage: DMC/Methanol, 1-8%, 25 CV). The desired product was obtained (1.82 g, yield: 94.2%) as a light-yellow solid; 1H NMR (500 MHz, CDCl3) delta 2.38 (s, 3H), 4.66 (s, 2H), 7.05 (s, 1H), 7.22 (m, 2H), 7.30 (m, 1H), 7.42 (d, 1H), 7.51 (d, 2H), 7.89 (m, 3H), 8.51 (m, 2H), 8.63 (s, 1H), 8.71 (d, 1H), 9.28 (s, IH). LC-MS (m/z) calculated, 429.14, found, 430.2 [M+H]+.
93%	In N,N-dimethyl-formamide; at 0℃; for 1h;	5mmol6-Methyl-N1-(4-(3-substituted-pyridine)2-substituted pyrimidine-)benzene-1,3-diamine compound iAnd 7 mmol of triethylamine (Et3N) was cooled to zero degrees Celsius in 15 mL of N,N-dimethylformamide (DMF).Under stirring,5.5 mmol of 4-(chloromethyl)benzoyl chloride was added in portions and the reaction was stirred at zero degrees Celsius for 1 hour.The reaction system was extracted with ethyl acetate, the organic phases were combined and dried over anhydrous sodium sulfate.The solvent was removed on a rotary evaporator and the residue was isolated on a silica gel column.4-(Chloromethyl)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide compound j (yield: 93) %).
86%	In N,N-dimethyl-formamide; at 0℃;Alkaline conditions;	6-methyl-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine (10) (5?mmol, 1.38?g) and DIEA (7.5?mmol, 968?mg) in 15?mL DMF at 0?C was added 4-(chloromethyl)benzoyl chloride (5.5?mmol, 1.03?g) dropwisely, and the solution was stirred at 0?C for 1?h. The system was quenched with water and extracted with EtOAc and dried with anhydrous Na2SO4. The solvents were removed under vacuum and the residue was purified by silica gel flash chromatography (EtOAc) to provide compound 11a (1.84?g, 86%). 1H NMR (400MHz, DMSO-d6) delta 10.29 (s, 1H), 9.29 (s, 1H), 8.98 (s, 1H), 8.69 (s, 1H), 8.52 (s, 2H), 8.12 (s, 1H), 7.99 (s, 2H), 7.70-7.33 (m, 5H), 7.22 (s, 1H), 4.85 (s, 2H), 2.24 (s, 3H). 13C NMR (101MHz, DMSO-d6): delta 164.95, 161.53, 161.08, 159.36, 151.21, 148.05, 140.83, 137.73, 137.05, 134.78, 134.43, 132.15, 130.00, 128.64,128.02, 127.64, 123.73, 117.23, 116.87, 107.51, 45.41, 17.60. HRMS (ESI, m/z) [M+H]+ calcd for C24H21ClN5O: 430.1435, found: 430.1436 [21].
68%	With triethylamine; In dichloromethane; at 0 - 20℃; for 18h;	a) Synthesis of compound 2a Compound 1a (5.0 g, 18.0 mmol; Manufacturer: Shanghai Xugang bio-tech limited company), and triethylamine (3.6 g, 35.6 mmol) were dissolved in dichloromethane (400 ml), 4-(chloromethyl)benzoyl chloride (4.0 g, 21.3 mmol) was dissolved in dichloromethane (100 ml), at 0 C, add the drops into the reaction solution, and end up to the room temperature, stir at room temperature for 18 hours, the solid precipitated, filtered and collected. Wash the solid with dichlomethane, then with water, to give the yellow solid compound 2a (5.3 g, 68% yield). 1H NMR (400 MHz, DMSO-d6): delta 10.23 (s, 1 H), 9.28 (s, 1 H), 8.97 (s, 1 H), 8.69 (d, J = 4.4 Hz, 1 H), 8.52 (m, 2 H), 8.09 (s, 1 H), 7.97 (d, J = 7.6 Hz, 2 H), 7.59-7.42 (m, 5 H), 7.22 (d, J = 8.0 Hz, 1 H), 4.84 (s, 2 H), 2.23 (s, 3 H). MS (ESI+) m/z: 430 [M +1]+.
67 - 70%	With triethylamine; In chloroform; at 0 - 5℃; for 4 - 5h;	Procedure : 80 L chloroform is charged into the reactor 12.8 Kgs of N-(5-amino~2-methylphenyl)-4-(3-pyridyl)~2-pyrimidine of the formula (VII) amine is charged into thereactor. Stirred for 15 minutes to get clear solution 9.3 Kg of triethylamine is charged.To the reaction mass 10.4 Kg of 4-(Chloromethyl)benzoyl chloride dissolved in 70 Lchloroform is charged slowly during 4-5 hours at 0-5C. The compound of the formula(II)is centrifuged and washed with 15 L DM water and 15 L Ethyl acetate, the product isdried at 60-70C.Yield: 13.9 Kg (70%)MR: 181-183C.Purity by TLC : Single spotStep-4 : Preparation of 4-(chloromethyl)-N-4-methyl-3-[(4-(3-pyridinyl)-2-pyritnidinyl]imino]phenyl benzamide (II)8 L chloroform is charged into the reactor 1.28 Kgs of N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine of the formula (VII) amine is charged into the ;tor. Stirred for 15 minutes to get clear solution 0.9 Kg of triethylamine is charged.the reaction mass 1.04 Kg of 4-(Chloromethyl)benzoyl chloride dissolved in 7 L)roform is charged slowly during 2 hours at 0-5C, The compound of the formulais centrifuged and washed with 2 L DM water and 2 L Ethyl acetate, the product isid at 60-70C.Id: 1.3 5 Kg (68%).: 180-182C.ity by TLC : Single spot Step-4 : Preparation of 4-(chloromethyl)-N_-4-methyl-3-[(4-(3-pyridinyl)-2-pyrimidinyl]aminojphenyl benzamide (II) L chloroform is charged into the reactor 1.28 Kgs of N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine of the formula (VII) amine is charged into thereactor. Stirred for 15 minutes to get clear solution 0.9 Kg of triethylamine is charged.To the reaction mass 1.04 Kg of 4-(Chloromethyl)benzoyl chloride dissolved in 7 Lchloroform is charged slowly during 3 hours at 5-10C. The compound of the formula(II)is centrifuged and washed with 2 L DM water and 2 L Ethyl acetate, the product isdried at 60-70C.Yield: 1.34 Kg (67%)MR: 180-182C.Purity by TLC : Single spotStep-4 : Preparation of 4-(chloromethyl)-TSf_-4-methyl-3-[(4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl benzamide (II)8 L chloroform is charged into the reactor 1.28 Kgs of N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine of the formula (VII) amine is charged into the reactor. Stirred for 15 minutes to get clear solution 0.9 Kg of triethylamine is charged. To the reaction mass 1.04 Kg of 4-(Chloromethyl)benzoyl chloride dissolved in 7 Lchloroform is charged slowly during 2 hours at 5-10C. The compound of the formula(II)is centrifuged and washed with 2 L DM water and 2 L Ethyl acetate, the product isdried at 60-70C.Yield: 1.36 Kg (68%)MR: 181-183C.Purity by TLC : Single spot
		N- (5-AMINO-2-METHYLPHENYL)-4- (3-PYRIDYL)-2-PYRIMIDINE-AMINE (2.83g, 8. 29MMOL) was dissolved in tetrahydrofuran (20MA), triethylamine (1. 4MA, 9.95mmol) was added thereto, and the mixture was stirred for 30 minutes. 4-CHLOROMETHYL benzoyl chloride (2.03g, 10.78mmol) was added and the whole mixture was reacted under reflux for 4 hours. The mixture was filtered, and the filtrate was concentrated and crystallized from water to give N- (5- (4-CHLOROMETHYLBENZOYLAMINO)-2-METHYLPHENYL)-4- (3-PYRIDYL)-2-PYRIMIDINE- amine (3.12g). Rf= 0. 38 (Methylene chloride : METHANOL = 9 : 1) IH-NMR (DMSO-D6) = 2.23 (s, 3H), 4.45 (s, 2H), 7.20-7. 24 (d, LH), 7.43-7. 61 (m, 5H), 7.94-7. 98 (d, LH), 8.09 (s, LH), 8.50-8. 53 (d, LH), 9.02 (s, LH), 9.28 (s, LH), 10.27 (s, LH)
	With triethylamine; In tetrahydrofuran; for 4.5h;Heating / reflux;	N- (5-AMINO-2-METHYLPHENYL)-4- (3-PYRIDYL)-2-PYRIMIDINE-AMINE (2.83g, 8. 29MMOL) was dissolved in tetrahydrofuran (20 M), triethylamine (1.4 M, 9. 95MMOL) was added thereto, and the mixture was stirred for 30 minutes. 4-Chloromethyl benzoyl chloride (2.03g, 10.78mmol) was added and the whole mixture was reacted under reflux for 4 hours. The mixture was filtered, and the filtrate was concentrated and crystallized FRCM water to give N- (5-(4-CHLORCMETHYLBENZOYLAMINO)-2-METHYLPHENYL)-4-(3-PYRIDYL)-2-PYRIMIDINE-AMINE (3.12g). [155] [156] R = 0.38 (Methylene chloride : Methanol = 9 : 1) f [157] H-NMR (DMSO-d) = 2.23 (s, 3H), 4.45 (s, 2H), 7.20-7. 24 (d, 1H), 7.43-7. 61 (m, 5H), 6 7.94-7. 98 (d, 1H), 8.09 (S, 1H), 8.50-8. 53 (d, 1H), 9.02 (s, 1H), 9.28 (s, 1H), 10. 27 (s, LH)
130 mg		N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine, THF (5mL) and TEA (0.2mL) were added to the reaction flask, cooled to 0 C and stirred for 10 minutes, then a solution of 4-chloromethylbenzoyl chloride (80 mg) in THF (2 ml) was slowly added dropwise. Into the above reaction solution. After stirring at 0 C for 2 hours, the reaction liquid was concentrated to a solid. Ethyl acetate (100 ml) was added and the solid was dissolved and washed with water (100 ml). The organic phase was concentrated again to give the product (130 mg).

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5
[ 110-91-8 ]
[ 110-85-0 ]
[ 5683-31-8 ]
[ 876-08-4 ]
[ 100-39-0 ]
{3-[4-(4-benzyl-piperazine-1-carbonyl)-benzyl]-3H-[1,2,3]triazol-4-yl}-morpholin-4-yl-methanone [ No CAS ]