8-Chloro-3-methoxy-1,7-naphthyridine → (2,3-difluoro-5-((3-methoxy-1,7-naphthyridin-8-yl)amino)phenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

HRID 930409Notes

Reaction equation

HRID 930409 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[N:24]=[CH:25][CH:26]=[C:27]2[C:32]=1[N:31]=[CH:30][C:29]([O:33][CH3:34])=[CH:28]2>>[F:20][C:5]1[C:4]([F:21])=[CH:3][C:2]([NH:1][C:23]2[N:24]=[CH:25][CH:26]=[C:27]3[C:32]=2[N:31]=[CH:30][C:29]([O:33][CH3:34])=[CH:28]3)=[CH:7][C:6]=1[C:8]1([CH3:19])[CH2:13][CH:12]([C:14]([F:17])([F:16])[F:15])[O:11][C:10]([NH2:18])=[N:9]1

Participants

3

Reactant 2

HCID 867157508-Chloro-3-methoxy-1,7-naphthyridine2×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 86732248(2,3-difluoro-5-((3-methoxy-1,7-naphthyridin-8-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 8-chloro-3-methoxy-1,7-naphthyridine (intermediate 31) in step 2. MS m/z=468.2 [M+H]+. Calculated for C21H18F5N5O2: 467.4

Sources & evidence

ORD record
ord-4121dbad72374b2a887c639af36984d8
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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