4,7-Dichloropyrido[3,2-d]pyrimidine → (4S,6S)-4-(5-((7-chloropyrido[3,2-d]pyrimidin-4-yl)amino)-2-fluoropyridin-3-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

HRID 930304Notes

Reaction equation

HRID 930304 reaction equation
[NH2:1][C:2]1[O:3][C@H:4]([C:26]([F:29])([F:28])[F:27])[CH2:5][C@:6]([C:9]2[CH:10]=[C:11]([NH:16][C:17](=O)[C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=3)[CH:12]=[N:13][C:14]=2[F:15])([CH3:8])[N:7]=1.ClC1C2N=CC(Cl)=CC=2[N:34]=[CH:35][N:36]=1>>[Cl:24][C:21]1[CH:20]=[N:19][C:18]2[C:17]([NH:16][C:11]3[CH:10]=[C:9]([C@:6]4([CH3:8])[CH2:5][C@@H:4]([C:26]([F:29])([F:28])[F:27])[O:3][C:2]([NH2:1])=[N:7]4)[C:14]([F:15])=[N:13][CH:12]=3)=[N:36][CH:35]=[N:34][C:23]=2[CH:22]=1

Participants

3

Reactant 2

HCID 714284454,7-Dichloropyrido[3,2-d]pyrimidine2×HCID 78321763N-(5-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-6-fluoropyridin-3-yl)-5-chloropicolinamide

Product 1

HCID 78320811(4S,6S)-4-(5-((7-chloropyrido[3,2-d]pyrimidin-4-yl)amino)-2-fluoropyridin-3-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

Procedure

The title compound was synthesized using steps and procedures analogous to those described in Method B (step 2) above, but using (4S,6S)-4-(5-amino-2-fluoropyridin-3-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (6a) and 4,7-dichloropyrido[3,2-d]pyrimidine (intermediate 9). MS m/z=456.0 [M+H]+. Calculated for C18H14ClF4N7O: 455.8

Sources & evidence

ORD record
ord-85aebccf54994e4ba22888477a9d287f
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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