Acetyl chloride → HCID 11215246, compound

HRID 1725656Notes

Reaction equation

HRID 1725656 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH:5]1([CH2:8][N:9]2[C:15](=[O:16])[C@@H:14]([NH:17][C:18]([N:20]3[CH2:25][CH2:24][CH:23]([N:26]4[CH:30]=[C:29]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[NH:28][C:27]4=[O:37])[CH2:22][CH2:21]3)=[O:19])[CH2:13][NH:12][C@H:11]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:10]2)[CH2:7][CH2:6]1.C(N(CC)CC)C>ClCCl>[C:1]([N:12]1[CH2:13][C@@H:14]([NH:17][C:18]([N:20]2[CH2:21][CH2:22][CH:23]([N:26]3[CH:30]=[C:29]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[NH:28][C:27]3=[O:37])[CH2:24][CH2:25]2)=[O:19])[C:15](=[O:16])[N:9]([CH2:8][CH:5]2[CH2:6][CH2:7]2)[CH2:10][C@@H:11]1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 68806096HCID 68806096, compound

Product 1

HCID 11215246HCID 11215246, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (2.1 □L, 0.03 mmol) was added to a solution of N-[(3R,6S)-1-(cyclopropylmethyl)-7-oxo-3-phenyl-1,4-diazepan-6-yl]-4-(2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)piperidine-1-carboxamide (16.9 mg, 0.03 mmol) and triethylamine (9 □L, 0.06 mmol) in dichloromethane (0.5 mL). After 30 min, the mixture was concentrated. Purification by silica gel chromatography (1% methanol/dichloromethane→5% methanol/dichloromethane) gave the title compound (17 mg). MS 571.3 (M+1).

Workup

  1. concentrationthe mixture was concentrated
  2. customPurification by silica gel chromatography (1% methanol/dichloromethane→5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-82b2aa4288c74ba895634aab66273c7f
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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