5-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid → HCID 71539604, compound

HRID 1915881Notes

Reaction equation

HRID 1915881 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 86680086HCID 86680086, compound

Product 1

HCID 71539604HCID 71539604, compound

Procedure

Following the procedure for Example 110 starting from (S)-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 lilac solid (53 mg, 31%). 1H NMR (400 MHz, CDCl3) δ 8.58 (s, 1H), 7.88 (s, 1H), 7.37-7.27 (m, 1H), 7.01 (t, J=8.8 Hz, 2H), 6.16 (s, 2H), 3.76 (s, 3H), 3.32 (t, J=11.3 Hz, 1H), 3.22 (t, J=9.3 Hz, 1H), 2.96 (t, J=12.9 Hz, 2H), 2.79 (d, J=11.0 Hz, 1H), 2.42-2.22 (m, 4H), 1.96 (t, J=10.2 Hz, 1H), 1.41-1.33 (m, 1H), 1.29-1.15 (m, 1H), 0.80 (t, J=7.5 Hz, 3H). LCMS (ES+) m/z 462 (M+1).

Sources & evidence

ORD record
ord-bec1382dcd4e447aaf7d1442806334f4
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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