5-Methyl-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-methylpyrazine-2-carboxamide

HRID 2045873Notes

Reaction equation

HRID 2045873 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][C:32]1[N:33]=[CH:34][C:35]([C:38](O)=[O:39])=[N:36][CH:37]=1>>[NH2:21][C:10]1[S:11][CH2:12][C@@H:13]2[C@@H:14]([C:17]([F:18])([F:20])[F:19])[O:15][CH2:16][C@:8]2([C:6]2[CH:7]=[C:2]([NH:1][C:38]([C:35]3[CH:34]=[N:33][C:32]([CH3:31])=[CH:37][N:36]=3)=[O:39])[CH:3]=[C:4]([F:30])[C:5]=2[F:29])[N:9]=1

Participants

3

Reactant 2

HCID 1228315-Methyl-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 57523871N-(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-methylpyrazine-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-methylpyrazine-2-carboxylic acid according to the general procedure. 1H NMR (400 MHz, CDCl3+MeOD) δ ppm 2.68 (s, 3H), 2.84 (dd, J=13.6, 3.8 Hz, 1H), 3.15 (dd, J=13.9, 3.0 Hz, 1H), 3.30-3.42 (m, 1H), 3.88 (d, J=10.4 Hz, 1H), 4.61 (d, J=8.6 Hz, 1H), 4.68 (quin, J=7.2 Hz, 1H), 7.13-7.25 (m, 1H), 8.05 (ddd, J=11.6, 6.8, 2.8 Hz, 1H), 8.46 (s, 1H), 9.30 (d, J=1.3 Hz, 1H)

Sources & evidence

ORD record
ord-dbe756cee6364639a8fc98be4b61a55d
Source dataset
uspto-grants-2013_11
Patent number
US08592408B2

Reaction notes

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