5-(1,1-Difluoroethyl)pyrazine-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-fluorophenyl)-5-(1,1-difluoroethyl)pyrazine-2-carboxamide

HRID 2195780Notes

Reaction equation

HRID 2195780 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][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:30][C:31]([C:34]1[N:35]=[CH:36][C:37]([C:40](O)=[O:41])=[N:38][CH:39]=1)([F:33])[CH3:32]>>[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:40]([C:37]3[CH:36]=[N:35][C:34]([C:31]([F:33])([F:30])[CH3:32])=[CH:39][N:38]=3)=[O:41])[CH:3]=[CH:4][C:5]=2[F:29])[N:9]=1

Participants

3

Reactant 2

HCID 668695495-(1,1-Difluoroethyl)pyrazine-2-carboxylic acidHCID 68171522tert-butyl[(4aS,5S,7aS)-7a-(5-amino-2-fluorophenyl)-5-trifluoromethyl-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl]carbamate

Product 1

HCID 57523783N-(3-((4aS,5S,7aS)-2-amino-5-(trifluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-(1,1-difluoroethyl)pyrazine-2-carboxamide

Procedure

Synthesized from tert-butyl [(4aS,5S,7aS)-7a-(5-amino-2-fluorophenyl)-5-trifluoromethyl-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl]carbamate and 5-(1,1-difluoroethyl)pyrazine-2-carboxylic acid according to the general procedure. 1H NMR (600 MHz, CDCl3) δ ppm 2.03 (t, J=18.8 Hz, 3H), 2.82 (d, J=12.0 Hz, 1H), 3.14 (d, J=12.4 Hz, 1H), 3.35-3.46 (m, 1H), 3.77-4.07 (m, 1H), 4.20-4.93 (m, 4H), 7.08 (dd, J=11.7, 9.0 Hz, 1H), 7.56 (d, J=4.5 Hz, 1H), 7.80-7.93 (m, 1H), 8.87 (s, 1 H), 9.43 (s, 1H), 9.59 (br. s., 1H)

Sources & evidence

ORD record
ord-95846744691443399b7ded9d7c1b93a2
Source dataset
uspto-grants-2012_12
Patent number
US08338407B2

Reaction notes

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