5-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid → HCID 71539920, compound

HRID 1915849Notes

Reaction equation

HRID 1915849 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH3:22])[C:6]=1[N:7]1[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][C@@H:8]1[CH2:20][CH3:21].C(OC([NH:30][C:31]1[S:35][C:34]([C:36]2[C:41]([F:42])=[CH:40][CH:39]=[CH:38][C:37]=2[F:43])=[N:33][C:32]=1[C:44](O)=[O:45])=O)(C)(C)C>>[NH2:30][C:31]1[S:35][C:34]([C:36]2[C:41]([F:42])=[CH:40][CH:39]=[CH:38][C:37]=2[F:43])=[N:33][C:32]=1[C:44]([NH:1][C:2]1[CH:3]=[N:4][N:5]([CH3:22])[C:6]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][C@@H:8]1[CH2:20][CH3:21])=[O:45]

Participants

3

Reactant 2

HCID 674381985-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acidHCID 86679972HCID 86679972, compound

Product 1

HCID 71539920HCID 71539920, compoundYield 19%

Procedure

Following the procedure for Example 112, reacting (S)-tert-butyl 4-(4-amino-1-methyl-1H-pyrazol-5-yl)-3-ethylpiperazine-1-carboxylate and 5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid from Example 25 gave 113 as a white solid (27 mg, 19% over two steps). 1H NMR (400 MHz, CDCl3) δ 8.68 (s, 1H), 7.91 (s, 1H), 7.31 (t, J=7.7 Hz, 1H), 7.03 (t, J=9.2 Hz, 2H), 6.20 (s, 2H), 3.77 (s, 3H), 3.24-3.14 (m, 2H), 3.12-2.93 (m, 4H), 2.60 (t, J=10.8 Hz, 1H), 1.48-1.28 (m, 1H), 1.28-1.16 (m, 1H), 0.79 (t, J=7.6 Hz, 3H). Alkyl NH not observed. LCMS (ES+) m/z 448 (M+1).

Sources & evidence

ORD record
ord-d74e955d2d7043a2b328628bebf3f307
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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