5-Cyano-3-methylpyridine-2-carboxylic acid → N-(3-((4S,6S)-2-Amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyano-3-methylpicolinamide

HRID 2178162Notes

Reaction equation

HRID 2178162 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C@:8]2([CH2:19][F:20])[CH2:13][C@@H:12]([C:14]([F:17])([F:16])[F:15])[O:11][C:10]([NH2:18])=[N:9]2)[CH:7]=1.[C:22]([C:24]1[CH:25]=[C:26]([CH3:33])[C:27]([C:30](O)=[O:31])=[N:28][CH:29]=1)#[N:23]>>[NH2:18][C:10]1[O:11][C@H:12]([C:14]([F:17])([F:15])[F:16])[CH2:13][C@:8]([C:6]2[CH:7]=[C:2]([NH:1][C:30](=[O:31])[C:27]3[C:26]([CH3:33])=[CH:25][C:24]([C:22]#[N:23])=[CH:29][N:28]=3)[CH:3]=[CH:4][C:5]=2[F:21])([CH2:19][F:20])[N:9]=1

Participants

3

Reactant 2

HCID 666658465-Cyano-3-methylpyridine-2-carboxylic acidHCID 86732112(4S,6S)-4-(5-amino-2-fluorophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

Product 1

HCID 71668047N-(3-((4S,6S)-2-Amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-cyano-3-methylpicolinamide

Procedure

The coupling of (4S,6S)-4-(5-amino-2-fluorophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (XI-2) and 5-cyano-3-methylpicolinic acid [S. Badiger et al. WO2011009943 (2011)] following General Procedure G yielded the title compound as a light yellow solid. MS: m/z=454.4 [M+H]+.

Sources & evidence

ORD record
ord-a57a6c7affff4baaa6e2cfe2fe374f27
Source dataset
uspto-grants-2015_06
Patent number
US09067926B2

Reaction notes

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