5-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid → HCID 51002101, compound

HRID 2088432Notes

Reaction equation

HRID 2088432 reaction equation
C(OC([NH:8][C:9]1[S:13][C:12]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])=[N:11][C:10]=1[C:22]([OH:24])=O)=O)(C)(C)C.[NH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1[N:32]1[CH2:37][CH2:36][CH2:35][C@H:34]([OH:38])[CH2:33]1>>[NH2:8][C:9]1[S:13][C:12]([C:14]2[C:15]([F:21])=[CH:16][CH:17]=[CH:18][C:19]=2[F:20])=[N:11][C:10]=1[C:22]([NH:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1[N:32]1[CH2:37][CH2:36][CH2:35][C@H:34]([OH:38])[CH2:33]1)=[O:24]

Participants

3

Reactant 2

HCID 674381985-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acidHCID 69812867HCID 69812867, compound

Product 1

HCID 51002101HCID 51002101, compoundYield 100%

Procedure

Followed the procedure as described in EXAMPLE 1, starting with 5-(tert-butoxycarbonylamino)-2-(2,6-bisfluorophenyl)thiazole-4-carboxylic acid and (S)-1-(3-aminopyridin-4-yl)piperidin-3-ol. Obtained the desired product as a white solid (111 mg, 100%). 1H NMR (400 MHz, DMSO) δ 9.37 (s, 1H), 9.30 (s, 1H), 8.21 (d, J=5.3 Hz, 1H), 7.67 (s, 2H), 7.59-7.47 (m, 1H), 7.29 (t, J=8.9 Hz, 2H), 7.14 (d, J=5.3 Hz, 1H), 4.81 (d, J=4.7 Hz, 2H), 3.81-3.63 (m, 3H), 3.19-3.07 (m, 1H), 2.99 (d, J=11.2 Hz, 1H), 2.61-2.33 (m, 2H), 1.90 (d, J=12.1 Hz, 1H), 1.71 (m, 3H), 1.30-1.09 (m, 2H). ESIMS m/z=432.2 (M+1).

Sources & evidence

ORD record
ord-15cfcacb5d4942f5becf9aa4b69e396d
Source dataset
uspto-grants-2013_05
Patent number
US08435976B2

Reaction notes

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