Benzyl Bromide → HCID 11342561, compound

HRID 1725655Notes

Reaction equation

HRID 1725655 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]1([CH2:10][N:11]2[C:17](=[O:18])[C@@H:16]([NH:19][C:20]([N:22]3[CH2:27][CH2:26][CH:25]([N:28]4[CH:32]=[C:31]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[NH:30][C:29]4=[O:39])[CH2:24][CH2:23]3)=[O:21])[CH2:15][NH:14][C@H:13]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:12]2)[CH2:9][CH2:8]1.[CH2:46](Br)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CC(C)=O>[CH2:46]([N:14]1[CH2:15][C@@H:16]([NH:19][C:20]([N:22]2[CH2:27][CH2:26][CH:25]([N:28]3[CH:32]=[C:31]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[NH:30][C:29]3=[O:39])[CH2:24][CH2:23]2)=[O:21])[C:17](=[O:18])[N:11]([CH2:10][CH:7]2[CH2:9][CH2:8]2)[CH2:12][C@@H:13]1[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 68806096HCID 68806096, compound

Product 1

HCID 11342561HCID 11342561, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (6.4 mg, 0.05 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 (12.2.0 mg, 0.023 mmol) and benzyl bromide (14 □L, 0.12 mmol) in acetone (0.5 mL). After 18 h, the mixture was concentrated. Purification by silica gel chromatography (1% methanol/dichloromethane→5% methanol/dichloromethane) gave the title compound (11 mg). MS 619.3 (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-042dfe5da7f14b0b8862a740c112953d
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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