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

HRID 930372Notes

Reaction equation

HRID 930372 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH3:12])[C:6]([C:9]([OH:11])=O)=[N:7][CH:8]=1)#[N:2].[NH2:13][C:14]1[CH:15]=[C:16]([C@:21]2([CH2:32][F:33])[CH2:26][C@@H:25]([C:27]([F:30])([F:29])[F:28])[O:24][C:23]([NH2:31])=[N:22]2)[C:17]([F:20])=[N:18][CH:19]=1>>[NH2:31][C:23]1[O:24][C@H:25]([C:27]([F:28])([F:30])[F:29])[CH2:26][C@:21]([C:16]2[CH:15]=[C:14]([NH:13][C:9](=[O:11])[C:6]3[C:5]([CH3:12])=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=3)[CH:19]=[N:18][C:17]=2[F:20])([CH2:32][F:33])[N:22]=1

Participants

3

Reactant 2

HCID 666658465-Cyano-3-methylpyridine-2-carboxylic acidHCID 86732195(4S,6S)-4-(5-amino-2-fluoropyridin-3-yl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

Product 1

HCID 86732198N-(5-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-6-fluoropyridin-3-yl)-5-cyano-3-methylpicolinamide

Procedure

The title compound was synthesized using procedures analogous to those described in Method H Step 2 (Example 66) above, but using 5-cyano-3-methylpicolinic acid and (4S,6S)-4-(5-amino-2-fluoropyridin-3-yl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (12k, as described in Example 138, method S). MS m/z=455.1 [M+H]+. Calculated for C19H15F5N6O2: 454.4

Sources & evidence

ORD record
ord-a8f3736aeb404d079d142e8ab13e9045
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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