2-Bromo-1,3-thiazole-4-carboxylic acid → tert-butyl ((3S,4R,7S)-7-(4-(2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-fluorooxepan-4-yl)carbamate

HRID 521890Notes

Reaction equation

HRID 521890 reaction equation
[Br:1][C:2]1[S:3][C:4](NC(=O)OC(C)(C)C)=[C:5]([C:7](=[O:31])[NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:30])[C:13]=2[C:14]23[O:21][CH:18]([CH2:19]C2)[CH:17]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:16][CH2:15]3)[N:6]=1.[F:40][C@H]1[C@H](NC(=O)OC(C)(C)C)CC[C@@H](C2N(C)N=CC=2[N+]([O-])=O)OC1.BrC1SC=C(C(O)=O)N=1>>[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:30])[C:13]=2[C@H:14]2[O:21][CH2:19][C@@H:18]([F:40])[C@H:17]([NH:22][C:23](=[O:24])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:16][CH2:15]2)=[O:31])[N:6]=1

Participants

4

Reactant 3

HCID 27632092-Bromo-1,3-thiazole-4-carboxylic acidHCID 86713819tert-butyl N-[2-bromo-4-[[5-[2-(tert-butoxycarbonylamino)-8-oxabicyclo[3.2.1]octan-5-yl]-1-methyl-pyrazol-4-yl]carbamoyl]thiazol-5-yl]carbamateHCID 86713841tert-butyl ((3S,4R,7S)-3-fluoro-7-(1-methyl-4-nitro-1H-pyrazol-5-yl)oxepan-4-yl)carbamate2×

Product 1

HCID 86713845tert-butyl ((3S,4R,7S)-7-(4-(2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-fluorooxepan-4-yl)carbamate

Procedure

Following the procedure for Intermediate 65, starting from tert-butyl ((3S,4R,7S)-3-fluoro-7-(1-methyl-4-nitro-1H-pyrazol-5-yl)oxepan-4-yl)carbamate (Intermediate 80) and replacing 2-bromo-5-(tert-butoxycarbonylamino)thiazole-4-carboxylic acid with 2-bromothiazole-4-carboxylic acid (commercial) gave tert-butyl ((3S,4R,7S)-7-(4-(2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-fluorooxepan-4-yl)carbamate.

Sources & evidence

ORD record
ord-f8f8b779634f457890f6a98efdf238db
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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