3,5-Difluoroaniline → (S)-tert-Butyl 4-(benzyloxy)-1-(3-bromo-2-(3,5-difluorophenylcarbamoyl)-1H-pyrrol-1-ylamino)-1-oxobutan-2-ylcarbamate

HRID 525042Notes

Reaction equation

HRID 525042 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:12]([NH:14][N:15]1[CH:19]=[CH:18][C:17]([Br:20])=[C:16]1[C:21]([O:23]C)=O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:33][C:34]1[CH:35]=[C:36]([CH:38]=[C:39]([F:41])[CH:40]=1)[NH2:37]>>[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:25][C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:32])[CH3:31])[C:12]([NH:14][N:15]1[CH:19]=[CH:18][C:17]([Br:20])=[C:16]1[C:21](=[O:23])[NH:37][C:36]1[CH:35]=[C:34]([F:33])[CH:40]=[C:39]([F:41])[CH:38]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 965953,5-DifluoroanilineHCID 86722060(S)-Methyl 1-(4-(benzyloxy)-2-(tert-butoxycarbonylamino)butanamido)-3-bromo-1H-pyrrole-2-carboxylate

Product 1

HCID 86722061(S)-tert-Butyl 4-(benzyloxy)-1-(3-bromo-2-(3,5-difluorophenylcarbamoyl)-1H-pyrrol-1-ylamino)-1-oxobutan-2-ylcarbamateYield 67.5%

Procedure

The title compound was prepared from (S)-methyl 1-(4-(benzyloxy)-2-(tert-butoxycarbonylamino)butanamido)-3-bromo-1H-pyrrole-2-carboxylate (4.0 g, 7.8 mmol) and 3,5-difluoroaniline (5.1 g, 39.0 mmol) following the experimental procedure described in Preparation 44a. 3.2 g (66% yield) of the desired compound were obtained.

Sources & evidence

ORD record
ord-62e0c269d5354c4db3b9ea32f7676c68
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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