3-Phenylcyclopentan-1-amine → [Bis-(4-methoxy-phenyl)-phenyl-methyl]-{(R)-5,5-difluoro-4-[2-fluoro-5-((1RS,3RS)-3-phenyl-cyclopentylamino)-phenyl]-4,6,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl}-amine

HRID 1626150Notes

Reaction equation

HRID 1626150 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.[C:44]1([CH:50]2[CH2:54][CH2:53][CH:52]([NH2:55])[CH2:51]2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>>[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:55][CH:52]4[CH2:53][CH2:54][CH:50]([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)[CH2:51]4)[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 30440783-Phenylcyclopentan-1-amineHCID 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 71008781[Bis-(4-methoxy-phenyl)-phenyl-methyl]-{(R)-5,5-difluoro-4-[2-fluoro-5-((1RS,3RS)-3-phenyl-cyclopentylamino)-phenyl]-4,6,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl}-amineYield 27%

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 (RS)-3-phenyl-cyclopentylamine (CAS [103858-37-3]; WO2007135026) yielded the title compound (27% yield) as a yellow solid. MS (ISP): m/z=734.5 [M+H]+.

Sources & evidence

ORD record
ord-62b98452b393442bac3b3cb2cbcad403
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

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