Hydroxylamine → ((1S,4S)-4-Amino-1-isopropylcyclopent-2-en-1-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone

HRID 901200Notes

Reaction equation

CC1[N:3]([C@H:8]2[CH2:12][C@:11]([C:16]([N:18]3[CH2:27][CH2:26][C:25]4[N:24]=[CH:23][C:22]([C:28]([F:31])([F:30])[F:29])=[CH:21][C:20]=4[CH2:19]3)=[O:17])([CH:13]([CH3:15])[CH3:14])[CH:10]=[CH:9]2)C(C)=CC=1.NO>>[CH:13]([C@@:11]1([C:16]([N:18]2[CH2:27][CH2:26][C:25]3[N:24]=[CH:23][C:22]([C:28]([F:31])([F:30])[F:29])=[CH:21][C:20]=3[CH2:19]2)=[O:17])[CH2:12][C@H:8]([NH2:3])[CH:9]=[CH:10]1)([CH3:15])[CH3:14]

Participants

Reactant 2

HCID 787Hydroxylamine

HCID 59700298((1S,4S)-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-isopropylcyclopent-2-enyl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone

Product 1

HCID 60122317((1S,4S)-4-Amino-1-isopropylcyclopent-2-en-1-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone

Procedure

treating the 6-{[(1S,4S)-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-isopropylcyclopent-2-en-1-yl]carbonyl}-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine with hydroxylamine to form (1S,4S)-4-isopropyl-4-{[3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl}cyclopent-2-en-1-amine; and

Sources & evidence

ORD record: ord-6e774990a7ff43c49401a6da5feb3001
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07361765B2

Reaction notes

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