5-Fluoro-3-pyridinamine → (S)-Benzyl 1-(3-bromo-2-(5-fluoropyridin-3-ylcarbamoyl)-1H-pyrrol-1-ylamino)-1-oxopropan-2-ylcarbamate

HRID 525031Notes

Reaction equation

HRID 525031 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH3:26])[C:13]([NH:15][N:16]1[CH:20]=[CH:19][C:18]([Br:21])=[C:17]1[C:22]([O:24]C)=O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:27][C:28]1[CH:29]=[C:30]([NH2:34])[CH:31]=[N:32][CH:33]=1>>[Br:21][C:18]1[CH:19]=[CH:20][N:16]([NH:15][C:13](=[O:14])[C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH3:26])[C:17]=1[C:22](=[O:24])[NH:34][C:30]1[CH:31]=[N:32][CH:33]=[C:28]([F:27])[CH:29]=1

Participants

3

Reactant 2

HCID 5744505-Fluoro-3-pyridinamineHCID 86722049(S)-Methyl 1-(2-(benzyloxycarbonylamino)propanamido)-3-Bromo-1H-Pyrrole-2-carboxylate

Product 1

HCID 86722050(S)-Benzyl 1-(3-bromo-2-(5-fluoropyridin-3-ylcarbamoyl)-1H-pyrrol-1-ylamino)-1-oxopropan-2-ylcarbamateYield 69.6%

Procedure

The title compound was prepared from (S)-methyl 1-(2-(benzyloxycarbonylamino)propanamido)-3-bromo-1H-pyrrole-2-carboxylate (2.00 g, 4.7 mmol) and 5-fluoropyridin-3-amine (4.23 g, 37.6 mmol) following the experimental procedure described in Preparation 44a. 1.65 g (69% yield) of the desired compound were obtained.

Sources & evidence

ORD record
ord-deb01e796426423abac4ede5fd4ab981
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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