5-Methoxypyridine-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-methoxypicolinamide

HRID 930374Notes

Reaction equation

HRID 930374 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([OH:11])=O)=[N:7][CH:8]=1.[NH2:12][C:13]1[CH:14]=[C:15]([C@:20]2([CH2:31][F:32])[CH2:25][C@@H:24]([C:26]([F:29])([F:28])[F:27])[O:23][C:22]([NH2:30])=[N:21]2)[C:16]([F:19])=[N:17][CH:18]=1>>[NH2:30][C:22]1[O:23][C@H:24]([C:26]([F:27])([F:29])[F:28])[CH2:25][C@:20]([C:15]2[CH:14]=[C:13]([NH:12][C:9](=[O:11])[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][N:7]=3)[CH:18]=[N:17][C:16]=2[F:19])([CH2:31][F:32])[N:21]=1

Participants

3

Reactant 2

HCID 119589395-Methoxypyridine-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 86732200N-(5-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-6-fluoropyridin-3-yl)-5-methoxypicolinamide

Procedure

The title compound was synthesized using procedures analogous to those described in Method H Step 2 (Example 66) above, but using 5-methoxy-picolinic acid and (4S,6S)-4-(5-amino-2-fluoropyridin-3-yl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (as described in Example 138, method S). MS m/z=446.0 [M+H]+. Calculated for C18H16F5N5O3: 445.3

Sources & evidence

ORD record
ord-793251a20dbc429083c7bdbdbdcf643a
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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