2-Bromo-5-((tert-butoxycarbonyl)amino)thiazole-4-carboxylic acid → tert-butyl 2-bromo-4-(1-(2,2-difluoroethyl)-5-(4-hydroxyazepan-1-yl)-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate

HRID 1915757Notes

Reaction equation

HRID 1915757 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH2:15][CH:16]([F:18])[F:17])[C:6]=1[N:7]1[CH2:13][CH2:12][CH2:11][CH:10]([OH:14])[CH2:9][CH2:8]1.[Br:19][C:20]1[S:21][C:22]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[C:23]([C:25](O)=[O:26])[N:24]=1>>[Br:19][C:20]1[S:21][C:22]([NH:28][C:29](=[O:30])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[C:23]([C:25](=[O:26])[NH:1][C:2]2[CH:3]=[N:4][N:5]([CH2:15][CH:16]([F:18])[F:17])[C:6]=2[N:7]2[CH2:13][CH2:12][CH2:11][CH:10]([OH:14])[CH2:9][CH2:8]2)[N:24]=1

Participants

3

Reactant 2

HCID 581821562-Bromo-5-((tert-butoxycarbonyl)amino)thiazole-4-carboxylic acidHCID 866799701-(4-amino-1-(2,2-difluoroethyl)-1H-pyrazol-5-yl)azepan-4-ol

Product 1

HCID 86679969tert-butyl 2-bromo-4-(1-(2,2-difluoroethyl)-5-(4-hydroxyazepan-1-yl)-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamateYield 69%

Procedure

Following the procedure for Intermediate 7 starting with 1-(4-amino-1-(2,2-difluoroethyl)-1H-pyrazol-5-yl)azepan-4-ol and 2-bromo-5-(tert-butoxycarbonylamino)-thiazole-4-carboxylic acid afforded tert-butyl 2-bromo-4-(1-(2,2-difluoroethyl)-5-(4-hydroxyazepan-1-yl)-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate as a colorless solid (265 mg, 69%). 1H NMR (400 MHz, CDCl3) δ 10.39 (s, 1H), 9.14 (s, 1H), 8.02 (s, 1H), 6.18 (tt, J=55.9, 4.5 Hz, 1H), 4.38-4.27 (m, 2H), 3.33-3.12 (m, 5H), 2.20 (br s, 1H), 2.35-1.58 (m, 4H), 1.70-1.48 (m, 2H).

Sources & evidence

ORD record
ord-a6690788ae6c47abb2d62476f880d724
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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