5-Chloro-2-methoxypyrido[3,4-b]pyrazine → (4S,6S)-4-(2,3-difluoro-5-((2-methoxypyrido[3,4-b]pyrazin-5-yl)amino)phenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

HRID 930408Notes

Reaction equation

HRID 930408 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([F:21])[C:5]([F:20])=[C:6]([C@:8]2([CH3:19])[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.Cl[C:23]1[C:28]2=[N:29][CH:30]=[C:31]([O:33][CH3:34])[N:32]=[C:27]2[CH:26]=[CH:25][N:24]=1>>[F:20][C:5]1[C:4]([F:21])=[CH:3][C:2]([NH:1][C:23]2[C:28]3=[N:29][CH:30]=[C:31]([O:33][CH3:34])[N:32]=[C:27]3[CH:26]=[CH:25][N:24]=2)=[CH:7][C:6]=1[C@:8]1([CH3:19])[CH2:13][C@@H:12]([C:14]([F:17])([F:16])[F:15])[O:11][C:10]([NH2:18])=[N:9]1

Participants

3

Reactant 2

HCID 867157445-Chloro-2-methoxypyrido[3,4-b]pyrazine2×HCID 86732244(4S,6S)-4-(5-amino-2,3-difluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

Product 1

HCID 86732247(4S,6S)-4-(2,3-difluoro-5-((2-methoxypyrido[3,4-b]pyrazin-5-yl)amino)phenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

Procedure

The titled compound was synthesized by procedure and steps analogous to those described in Method B, Example 8 above, but using (4S,6S)-4-(5-amino-2,3-difluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (17i, Example 163, Method Y, step 9) and 5-chloro-2-methoxypyrido[3,4-b]pyrazine (intermediate 3) in step 2. MS m/z=469.1 [M+H]+. Calculated for C20H17F5N6O2: 468.4

Sources & evidence

ORD record
ord-e7471050bcff49fea9e9345112bd31ae
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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