8-Chloro-5-fluoro-1,7-naphthyridine-3-carbonitrile → 8-((3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4,5-difluorophenyl)amino)-5-fluoro-1,7-naphthyridine-3-carbonitrile

HRID 930407Notes

Reaction equation

HRID 930407 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][C:26]([F:35])=[C:27]2[C:32]=1[N:31]=[CH:30][C:29]([C:33]#[N:34])=[CH:28]2>>[NH2:18][C:10]1[O:11][C@H:12]([C:14]([F:17])([F:16])[F:15])[CH2:13][C@:8]([C:6]2[CH:7]=[C:2]([NH:1][C:23]3[N:24]=[CH:25][C:26]([F:35])=[C:27]4[C:32]=3[N:31]=[CH:30][C:29]([C:33]#[N:34])=[CH:28]4)[CH:3]=[C:4]([F:21])[C:5]=2[F:20])([CH3:19])[N:9]=1

Participants

3

Reactant 2

HCID 867158748-Chloro-5-fluoro-1,7-naphthyridine-3-carbonitrile2×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 867322468-((3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4,5-difluorophenyl)amino)-5-fluoro-1,7-naphthyridine-3-carbonitrile

Procedure

The titled compound was synthesized by procedure and steps analogous to those described in Method B, Step 2, 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-5-fluoro-1,7-naphthyridine-3-carbonitrile (intermediate 17) in step 2. MS m/z=481.1 [M+H]+. Calculated for C21H14F6N6O: 480.4

Sources & evidence

ORD record
ord-2ae2c4a63fcb46de887f567f4b97fffa
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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