Benzoyl chloride → HCID 67283224, compound

HRID 1910707Notes

Reaction equation

HRID 1910707 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]3[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:10]=3[N:11]([CH3:27])[C:12](=[O:26])[CH:13]([CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)[N:14]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:40](Cl)(=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>ClCCl>[Cl:32][C:30]1[CH:29]=[CH:28][C:10]2[N:11]([CH3:27])[C:12](=[O:26])[CH:13]([CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)[N:14]=[C:8]([N:5]3[CH2:4][CH2:3][CH:2]([NH:1][C:40](=[O:47])[C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[CH2:7][CH2:6]3)[C:9]=2[CH:31]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 67282603HCID 67282603, compound

Product 1

HCID 67283224HCID 67283224, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-(4-Aminopiperidin-1-yl)-7-chloro-1-methyl-3-(naphthalen-2-ylmethyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (50 mg, 0.11 mmol) was dissolved in dichloromethane (2 mL) and triethylamine (31 μL, 0.22 mmol), a solution of benzoyl chloride (10 μL, 0.11 mmol) in dichloromethane (0.2 mL) was added dropwise, and stirred at ambient temperature for 30 minutes. To the solution was added silica gel and the mixture was concentrated. Column chromatography eluting with a gradient of 50-100% ethyl acetate in hexanes provided N-(1-(7-chloro-1-methyl-3-(naphthalen-2-ylmethyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)piperidin-4-yl)benzamide (35 mg, 57% yield). ESI m/z measured 551.2224 [M+H]+. calculated 551.2214.

Workup

  1. additionTo the solution was added silica gel
  2. concentrationthe mixture was concentrated
  3. washColumn chromatography eluting with a gradient of 50-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-292e9029d6e1460d86bf557e17e889ff
Source dataset
uspto-grants-2013_12
Patent number
US08604023B2

Reaction notes

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