O-Toluidine → [Bis-(4-methoxy-phenyl)-phenyl-methyl]-[(R)-5,5-difluoro-4-(2-fluoro-5-o-tolylamino-phenyl)-4,6,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl]-amine

HRID 1626146Notes

Reaction equation

HRID 1626146 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:24][C:25]2[O:26][C:27]([CH3:43])([CH3:42])[C:28]([F:41])([F:40])[C@:29]([C:32]3[CH:37]=[C:36](Br)[CH:35]=[CH:34][C:33]=3[F:39])([CH3:31])[N:30]=2)([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[CH3:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][C:50]=1[NH2:51]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:24][C:25]2[O:26][C:27]([CH3:43])([CH3:42])[C:28]([F:41])([F:40])[C@:29]([C:32]3[CH:37]=[C:36]([NH:51][C:50]4[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=4[CH3:44])[CH:35]=[CH:34][C:33]=3[F:39])([CH3:31])[N:30]=2)([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 7242O-ToluidineHCID 58304193[bis-(4-methoxy-phenyl)-phenyl-methyl]-[(R)-4-(5-bromo-2-fluoro-phenyl)-5,5-difluoro-4,6,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl]-amine

Product 1

HCID 71009100[Bis-(4-methoxy-phenyl)-phenyl-methyl]-[(R)-5,5-difluoro-4-(2-fluoro-5-o-tolylamino-phenyl)-4,6,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl]-amineYield 55%

Procedure

In a manner analogous to that described in Example 3 a), the amination of [bis-(4-methoxy-phenyl)-phenyl-methyl]-[(R)-4-(5-bromo-2-fluoro-phenyl)-5,5-difluoro-4,6,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl]-amine (intermediate C4.1) with o-tolylamine yielded the title compound (55% yield) as a pale red foam. MS (ISP): m/z=680.4 [M+H]+.

Sources & evidence

ORD record
ord-0ffa98c0b82a4dfca3735355f19fca0c
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

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