5-Methoxypyridine-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-methoxypicolinamide

HRID 1429638Notes

Reaction equation

HRID 1429638 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]=[CH:23][C:22]=2[F:28])[N:13]=1)(C)(C)C.[CH3:30][O:31][C:32]1[CH:33]=[CH:34][C:35]([C:38](O)=[O:39])=[N:36][CH:37]=1>>[NH2:7][C:8]1[S:9][CH2:10][C@@H:11]2[C@@H:16]([C:17]([F:19])([F:20])[F:18])[O:15][CH2:14][C@:12]2([C:21]2[CH:26]=[C:25]([NH:27][C:38](=[O:39])[C:35]3[CH:34]=[CH:33][C:32]([O:31][CH3:30])=[CH:37][N:36]=3)[CH:24]=[CH:23][C:22]=2[F:28])[N:13]=1

Participants

3

Reactant 2

HCID 119589395-Methoxypyridine-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 57525006N-(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-methoxypicolinamide

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-methoxypyridine-2-carboxylic acid according to the general procedure. 1H NMR (400 MHz, CDCl3) δ ppm 2.88 (dd, J=13.8, 3.7 Hz, 1 H), 3.23 (dd, J=13.8, 2.4 Hz, 1 H), 3.46 (d, J=7.3 Hz, 1 H), 3.89-4.02 (m, 4 H), 4.54-5.00 (m, 4 H), 7.11 (dd, J=11.9, 8.8 Hz, 1 H), 7.36 (dd, J=8.8, 2.8 Hz, 1 H), 7.61 (dd, J=7.1, 2.8 Hz, 1 H), 7.97 (dt, J=8.5, 3.6 Hz, 1 H), 8.23-8.30 (m, 2 H), 9.86 (s, 1 H)

Sources & evidence

ORD record
ord-0c832f3b83734948938c952994c1c5f4
Source dataset
uspto-grants-2015_01
Patent number
US08940734B2

Reaction notes

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