Bromoacetyl bromide → HCID 58641422, compound

HRID 1394941Notes

Reaction equation

HRID 1394941 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[CH:6]1([C@H:9]([NH2:31])[C:10]([N:12]2[CH2:16][C:15]([C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=3[F:24])=[CH:14][C@H:13]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:11])[CH2:8][CH2:7]1.C(N(CC)C(C)C)(C)C>ClCCl>[Br:1][CH2:2][C:3]([NH:31][C@@H:9]([CH:6]1[CH2:8][CH2:7]1)[C:10]([N:12]1[CH2:16][C:15]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])=[CH:14][C@H:13]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:11])=[O:4]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 81531DiisopropylethylamineHCID 6102824HCID 6102824, compound

Product 1

HCID 58641422HCID 58641422, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromoacetyl bromide (49 μL, 0.56 mmol, 1.1 equiv) was added to a solution of (1S)-1-cyclopropyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethanamine (16-7, 181 mg, 0.511 mmol, 1 equiv) and N,N-diisopropylethylamine (107 μL, 0.613 mmol, 1.20 equiv) in dichloromethane (10 mL) at 23° C., and the resulting mixture was allowed to stir for 30 minutes. The reaction mixture was partitioned between water (70 mL) and dichloromethane (2×60 mL). The combined organic layers were dried over sodium sulfate and concentrated to give 2-bromo-N-{(1S)-1-cyclopropyl-2-[(2S) (2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethyl}acetamide (25-1) as a pink foam. LRMS m/z (M+H) 477.3 found, 477.1 required.

Workup

  1. customThe reaction mixture was partitioned between water (70 mL) and dichloromethane (2×60 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a985f4f707b6456d919c48fe16615c66
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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