5-Methoxy-2-pyrazinecarboxylic 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-methoxypyrazine-2-carboxamide

HRID 2045872Notes

Reaction equation

HRID 2045872 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.[CH3:31][O:32][C:33]1[N:34]=[CH:35][C:36]([C:39]([OH:41])=O)=[N:37][CH:38]=1>>[NH2:21][C:10]1[S:11][CH2:12][C@@H:13]2[C@@H:14]([C:17]([F:19])([F:18])[F:20])[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]([O:32][CH3:31])=[CH:38][N:37]=3)=[O:41])[CH:3]=[C:4]([F:30])[C:5]=2[F:29])[N:9]=1

Participants

3

Reactant 2

HCID 457898115-Methoxy-2-pyrazinecarboxylic 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 57523870N-(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-methoxypyrazine-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-methoxypyrazine-2-carboxylic acid according to the general procedure. 1H NMR (400 MHz, CDCl3+MeOD) δ ppm 2.83 (dd, J=13.9, 3.8 Hz, 1H), 3.14 (dd, J=13.9, 3.0 Hz, 1H), 3.29-3.39 (m, 1H), 3.87 (d, J=8.3 Hz, 1H), 4.04 (s, 3H), 4.60 (d, J=8.3 Hz, 1H), 4.67 (quin, J=6.3 Hz, 1H), 7.11-7.21 (m, 1H), 8.03 (ddd, J=11.6, 6.9, 2.7 Hz, 1H), 8.15 (d, J=1.3 Hz, 1H), 8.96 (d, J=1.3 Hz, 1H)

Sources & evidence

ORD record
ord-037d43a5d078476297c0e8f473e83dad
Source dataset
uspto-grants-2013_11
Patent number
US08592408B2

Reaction notes

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