5-Chloro-2-picolinic 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-chloropicolinamide

HRID 930371Notes

Reaction equation

HRID 930371 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[NH2:11][C:12]1[CH:13]=[C:14]([C@:19]2([CH2:30][F:31])[CH2:24][C@@H:23]([C:25]([F:28])([F:27])[F:26])[O:22][C:21]([NH2:29])=[N:20]2)[C:15]([F:18])=[N:16][CH:17]=1>>[NH2:29][C:21]1[O:22][C@H:23]([C:25]([F:26])([F:28])[F:27])[CH2:24][C@:19]([C:14]2[CH:13]=[C:12]([NH:11][C:8](=[O:10])[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=3)[CH:17]=[N:16][C:15]=2[F:18])([CH2:30][F:31])[N:20]=1

Participants

3

Reactant 2

HCID 27628725-Chloro-2-picolinic 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 86732197N-(5-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-6-fluoropyridin-3-yl)-5-chloropicolinamide

Procedure

The title compound was synthesized using procedures analogous to those described in Method H Step 2 (Example 66) above, but using 5-chloropicolinic 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=449.9 [M+H]+. Calculated for C17H13ClF5N5O2: 449.8

Sources & evidence

ORD record
ord-44f7e6ed77c84c1490c1af49f11058c5
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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