5-Difluoromethympyrazine-2-carboxylic acid → N-(3-((4aS,5S,7aS)-2-amino-5-(trifluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-7a-yl)-4,5-difluorophenyl)-5-(difluoromethyl)pyrazine-2-carboxamide

HRID 2045871Notes

Reaction equation

HRID 2045871 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([F:30])[C:5]([F:29])=[C:6]([C@:8]23[CH2:16][O:15][C@H:14]([C:17]([F:20])([F:19])[F:18])[C@H:13]2[CH2:12][S:11][C:10]([NH:21]C(=O)OC(C)(C)C)=[N:9]3)[CH:7]=1.[F:31][CH:32]([F:42])[C:33]1[N:34]=[CH:35][C:36]([C:39](O)=[O:40])=[N:37][CH:38]=1>>[NH2:21][C:10]1[S:11][CH2:12][C@@H:13]2[C@@H:14]([C:17]([F:20])([F:19])[F:18])[O:15][CH2:16][C@:8]2([C:6]2[CH:7]=[C:2]([NH:1][C:39]([C:36]3[CH:35]=[N:34][C:33]([CH:32]([F:42])[F:31])=[CH:38][N:37]=3)=[O:40])[CH:3]=[C:4]([F:30])[C:5]=2[F:29])[N:9]=1

Participants

3

Reactant 2

HCID 574685755-Difluoromethympyrazine-2-carboxylic acidHCID 68171526tert-butyl [(4aS,5S,7aS)-7a-(5-amino-2,3-difluorophenyl)-5-trifluoromethyl-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl]carbamate

Product 1

HCID 57523786N-(3-((4aS,5S,7aS)-2-amino-5-(trifluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-7a-yl)-4,5-difluorophenyl)-5-(difluoromethyl)pyrazine-2-carboxamide

Procedure

Synthesized from tert-butyl [(4aS,5S,7aS)-7a-(5-amino-2,3-difluorophenyl)-5-trifluoromethyl-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl]carbamate and 5-difluoromethyl-pyrazine-2-carboxylic acid according to the general procedure. 1H NMR (400 MHz, CDCl3) δ ppm 2.90 (dd, J=13.8, 3.7 Hz, 1H), 3.19 (dd, J=13.8, 2.7 Hz, 1H), 3.31-3.49 (m, 1H), 3.95 (d, J=7.6 Hz, 1H), 4.44-5.15 (m, 4H), 6.81 (t, J=55.8 Hz, 4H), 7.22-7.35 (m, 1H), 8.08 (ddd, J=11.2, 6.8, 2.7 Hz, 1H), 8.94 (s, 1H), 9.53 (s, 1H), 9.67 (s, 1H)

Sources & evidence

ORD record
ord-8c94dd91199f4efa8c7431f9f30a59ce
Source dataset
uspto-grants-2013_11
Patent number
US08592408B2

Reaction notes

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