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 1429641Notes

Reaction equation

HRID 1429641 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][CH2:10][C@@H:11]2[C@@H:16]([C:17]([F:20])([F:19])[F:18])[O:15][CH2:14][C@:12]2([C:21]2[CH:26]=[C:25]([NH2:27])[CH:24]=[C:23]([F:28])[C:22]=2[F:29])[N:13]=1)(C)(C)C.[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>>[NH2:7][C:8]1[S:9][CH2:10][C@@H:11]2[C@@H:16]([C:17]([F:19])([F:18])[F:20])[O:15][CH2:14][C@:12]2([C:21]2[CH:26]=[C:25]([NH:27][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:24]=[C:23]([F:28])[C:22]=2[F:29])[N:13]=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, 1 H), 3.19 (dd, J=13.8, 2.7 Hz, 1 H), 3.31-3.49 (m, 1 H), 3.95 (d, J=7.6 Hz, 1 H), 4.44-5.15 (m, 4 H), 6.81 (t, J=55.8 Hz, 4 H), 7.22-7.35 (m, 1 H), 8.08 (ddd, J=11.2, 6.8, 2.7 Hz, 1 H), 8.94 (s, 1 H), 9.53 (s, 1 H), 9.67 (s, 1 H)

Sources & evidence

ORD record
ord-137f95dd6a374ee983cae1ccdbc6194a
Source dataset
uspto-grants-2015_01
Patent number
US08940734B2

Reaction notes

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