5-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid → HCID 71539603, compound

HRID 1915882Notes

Reaction equation

HRID 1915882 reaction equation
[CH2:1]([C@@H:3]1[CH2:8][N:7]([CH3:9])[CH2:6][CH2:5][N:4]1[C:10]1[N:14]([CH3:15])[N:13]=[CH:12][C:11]=1[NH2:16])[CH3:2].C(OC([NH:24][C:25]1[S:29][C:28]([C:30]2[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:31]=2[F:37])=[N:27][C:26]=1[C:38](O)=[O:39])=O)(C)(C)C>>[NH2:24][C:25]1[S:29][C:28]([C:30]2[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:31]=2[F:37])=[N:27][C:26]=1[C:38]([NH:16][C:11]1[CH:12]=[N:13][N:14]([CH3:15])[C:10]=1[N:4]1[CH2:5][CH2:6][N:7]([CH3:9])[CH2:8][C@H:3]1[CH2:1][CH3:2])=[O:39]

Participants

3

Reactant 2

HCID 674381985-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acidHCID 86680087HCID 86680087, compound

Product 1

HCID 71539603HCID 71539603, compoundYield 28%

Procedure

Following the procedure for Example 110, (R)-5-(2-ethyl-4-methylpiperazin-1-yl)-1-methyl-1H-pyrazol-4-amine and 5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid from Example 25 gave 176 as a white solid (47 mg, 28% over two steps). 1H NMR (400 MHz, CDCl3) δ 8.58 (s, 1H), 7.87 (s, 1H), 7.37-7.25 (m, 1H), 7.01 (t, J=8.8 Hz, 2H), 6.17 (s, 2H), 3.76 (s, 3H), 3.33 (t, J=11.3 Hz, 1H), 3.22 (t, J=9.2 Hz, 1H), 2.97 (t, J=12.7 Hz, 2H), 2.79 (d, J=11.0 Hz, 1H), 2.41-2.22 (m, 4H), 1.96 (t, J=10.2 Hz, 1H), 1.41-1.33 (m, 1H), 1.28-1.13 (m, 1H), 0.80 (t, J=7.5 Hz, 3H). LCMS (ES+) m/z 462 (M+1).

Sources & evidence

ORD record
ord-c82bf7fea80d4a0f8ccd7dd15465fd81
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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