5-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid → HCID 74983273, compound

HRID 1915948Notes

Reaction equation

HRID 1915948 reaction equation
[CH3:1][O:2][C:3]1([CH2:18][NH:19]C(=O)OC(C)(C)C)[CH2:8][CH2:7][N:6]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][C:10]=2[N+:15]([O-])=O)[CH2:5][CH2:4]1.C(OC([NH:34][C:35]1[S:39][C:38]([C:40]2[C:45]([F:46])=[CH:44][CH:43]=[CH:42][C:41]=2[F:47])=[N:37][C:36]=1[C:48](O)=[O:49])=O)(C)(C)C>>[NH2:34][C:35]1[S:39][C:38]([C:40]2[C:45]([F:46])=[CH:44][CH:43]=[CH:42][C:41]=2[F:47])=[N:37][C:36]=1[C:48]([NH:15][C:10]1[CH:11]=[N:12][N:13]([CH3:14])[C:9]=1[N:6]1[CH2:5][CH2:4][C:3]([CH2:18][NH2:19])([O:2][CH3:1])[CH2:8][CH2:7]1)=[O:49]

Participants

3

Reactant 2

HCID 674381985-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acidHCID 86680146HCID 86680146, compound

Product 1

HCID 74983273HCID 74983273, compoundYield 7%

Procedure

Following the procedure for Example 101 starting from tert-butyl (4-methoxy-1-(1-methyl-4-nitro-1H-pyrazol-5-yl)piperidin-4-yl)methylcarbamate and 5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)-thiazole-4-carboxylic acid gave 458 as an off-white solid (30 mg, 7% over three steps). 1H NMR (400 MHz, d4-MeOD) δ 8.56 (s, 1H), 7.56-7.42 (m, 2H), 7.15 (t, J=8.7 Hz, 2H), 3.74 (s, 3H), 3.42-3.33 (m, 4H), 3.23 (s, 2H), 3.12-2.95 (m, 3H), 1.97 (d, J=13.6 Hz, 2H), 1.76-1.66 (m, 2H). LCMS (ES+) m/z 478 (M+1)

Sources & evidence

ORD record
ord-cc23245125164722b32b5c160f231673
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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