HCID 67060934, compound → (1aR,5aR)-2-(2,4-Difluoro-phenyl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic Acid [1-((R)-2-(S)-methyl-5-methyl-pyrrolidine-1-carbonyl)-cyclopentyl]-amide

HRID 1623932Notes

Reaction equation

Cl.[NH2:2][C:3]1([C:8]([N:10]2[C@@H:14]([CH3:15])[CH2:13][CH2:12][C@H:11]2[CH3:16])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[N:25]1[C:32]2[C@@H:31]3[CH2:33][C@@H:30]3[CH2:29][C:28]=2[C:27]([C:34](O)=[O:35])=[N:26]1>>[CH3:16][C@H:11]1[CH2:12][CH2:13][C@@H:14]([CH3:15])[N:10]1[C:8]([C:3]1([NH:2][C:34]([C:27]2[C:28]3[CH2:29][C@H:30]4[CH2:33][C@H:31]4[C:32]=3[N:25]([C:19]3[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:18]=3[F:17])[N:26]=2)=[O:35])[CH2:7][CH2:6][CH2:5][CH2:4]1)=[O:9]

Participants

Reactant 2

HCID 67060934HCID 67060934, compound

HCID 68182595HCID 68182595, compound

Product 1

HCID 86669675(1aR,5aR)-2-(2,4-Difluoro-phenyl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic Acid [1-((R)-2-(S)-methyl-5-methyl-pyrrolidine-1-carbonyl)-cyclopentyl]-amide

Procedure

The title compound was prepared in a manner similar to that described in Method G using (1-aminocyclopentyl)((2R,5S)-2,5-dimethylpyrrolidin-1-yl)methanone hydrochloride and (1aR,5aR)-2-(2,4-Difluoro-phenyl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid. LCMS m/z=469.5 [M+H]+; 1H NMR (400 MHz, CD3CN) δ ppm 0.39-0.43 (m, 1H), 0.89-1.27 (m, 8H), 1.57-1.69 (m, 7H), 1.96-2.11 (m, 1H), 2.13-2.18 (m, 3H), 2.23-2.30 (m, 1H), 2.52-2.70 (m, 1H), 2.80 (d, J=17.2 Hz, 1H), 2.91 (dd, J=16.6, 6.6 Hz, 1H), 3.93-4.39 (m, 2H), 7.13-7.25 (m, 3H), 7.72 (td, J=8.8, 5.9 Hz, 1H).

Sources & evidence

ORD record: ord-5493f7b994e040c58d115603d4e3b600
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778950B2

Reaction notes

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