5-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid → HCID 74983226, compound

HRID 1915926Notes

Reaction equation

HRID 1915926 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH3:24])[C:6]=1[N:7]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][CH3:16])[CH:10]([NH:17]C(=O)C(F)(F)F)[CH2:9][CH2:8]1.C(OC([NH:32][C:33]1[S:37][C:36]([C:38]2[C:43]([F:44])=[CH:42][CH:41]=[CH:40][C:39]=2[F:45])=[N:35][C:34]=1[C:46](O)=[O:47])=O)(C)(C)C>>[NH2:32][C:33]1[S:37][C:36]([C:38]2[C:43]([F:44])=[CH:42][CH:41]=[CH:40][C:39]=2[F:45])=[N:35][C:34]=1[C:46]([NH:1][C:2]1[CH:3]=[N:4][N:5]([CH3:24])[C:6]=1[N:7]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][CH3:16])[CH:10]([NH2:17])[CH2:9][CH2:8]1)=[O:47]

Participants

3

Reactant 2

HCID 674381985-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acidHCID 86680126HCID 86680126, compound

Product 1

HCID 74983226HCID 74983226, compoundYield 60%

Procedure

Following the procedure for Example 107, starting from N-(1-(4-amino-1-methyl-1H-pyrazol-5-yl)-5-ethoxyazepan-4-yl)-2,2,2-trifluoroacetamide and 5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)-thiazole-4-carboxylic acid gave 385 as a brown solid (127 mg, 60% over two steps). 1H NMR (400 MHz, CDCl3) δ 8.61 (s, 1H), 7.85 (s, 1H), 7.42-7.28 (m, 1H), 7.04 (t, J=8.9 Hz, 2H), 6.19 (s, 2H), 3.78-3.58 (m, 4H), 3.47-3.35 (m, 1H), 3.38-3.25 (m, 2H), 3.25-3.16 (m, 3H), 3.09-3.01 (m, 1H), 2.13 (d, J=14.7 Hz, 1H), 2.00 (d, J=14.7 Hz, 1H), 1.92-1.82 (m, 1H), 1.84-1.58 (m, 3H), 1.22 (t, J=7.0 Hz, 3H). LCMS (ES+) m/z 492 (M+1)

Sources & evidence

ORD record
ord-8971b6b364004d03b35839f70cb6f1cc
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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