5-((Tert-butoxycarbonyl)amino)-2-(2-fluorophenyl)thiazole-4-carboxylic acid → HCID 74983241, compound

HRID 1915935Notes

Reaction equation

HRID 1915935 reaction equation
[CH3:1][C:2]1([NH:18]C(=O)OC(C)(C)C)[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][C:10]=2[N+:15]([O-])=O)[CH2:4][CH2:3]1.C(OC([NH:33][C:34]1[S:38][C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[F:45])=[N:36][C:35]=1[C:46](O)=[O:47])=O)(C)(C)C>>[NH2:33][C:34]1[S:38][C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[F:45])=[N:36][C:35]=1[C:46]([NH:15][C:10]1[CH:11]=[N:12][N:13]([CH3:14])[C:9]=1[N:5]1[CH2:6][CH2:7][CH2:8][C:2]([NH2:18])([CH3:1])[CH2:3][CH2:4]1)=[O:47]

Participants

3

Reactant 2

HCID 674367135-((Tert-butoxycarbonyl)amino)-2-(2-fluorophenyl)thiazole-4-carboxylic acidHCID 86680135HCID 86680135, compound

Product 1

HCID 74983241HCID 74983241, compoundYield 74%

Procedure

Following the procedure for Example 101 starting from tert-butyl 4-methyl-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)azepan-4-ylcarbamate and 5-(tert-butoxycarbonyl-amino)-2-(2-fluorophenyl)thiazole-4-carboxylic acid gave 412 as a pale brown solid (87 mg, 74% over three steps). 1H NMR (400 MHz, CDCl3) δ 8.73 (s, 1H), 8.13 (t, J=7.7 Hz, 1H), 7.85 (s, 1H), 7.39-7.30 (m, 1H), 7.26-7.11 (m, 2H), 6.11 (s, 2H), 3.75 (s, 3H), 3.40-3.18 (m, 3H), 3.17-3.09 (m, 1H), 1.98-1.89 (m, 1H), 1.90-1.71 (m, 5H), 1.23 (s, 3H). Exchangeable NH2 not observed. LCMS (ES+) m/z 444 (M+1)

Sources & evidence

ORD record
ord-cbdd7bed383342d798f48dfd5c5f93a7
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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