(3bS,4aR)-5,5-Difluoro-3b,4,4a,5-tetrahydro-3-(trifluoromethyl)-1H-cyclopropa(3,4)cyclopenta(1,2-c)pyrazole-1-acetic acid → N-((S)-1-(3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)-6-((2-hydroxyethyl)(methyl)amino)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)-2-((3bS,4aR)-5,5-difluoro-3-(trifluoromethyl)-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)acetamide

HRID 2170400Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C@@H:22]([NH:32][C:33](=[O:49])[CH2:34][N:35]3[C:39]4[C:40]([F:45])([F:44])[C@@H:41]5[CH2:43][C@@H:42]5[C:38]=4[C:37]([CH:46]([F:48])[F:47])=[N:36]3)[CH2:23][C:24]3[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=3)=[N:13][C:14]([N:17]([CH2:19][CH2:20][OH:21])[CH3:18])=[CH:15][CH:16]=2)=[C:7]2[C:3]=1[C:4]([NH:51][S:52]([CH3:55])(=[O:54])=[O:53])=[N:5][N:6]2[CH3:50].[F:56]C1(F)C2N(CC(O)=O)N=C(C(F)(F)F)C=2[C@H]2C[C@@H]12>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C@@H:22]([NH:32][C:33](=[O:49])[CH2:34][N:35]3[C:39]4[C:40]([F:44])([F:45])[C@@H:41]5[CH2:43][C@@H:42]5[C:38]=4[C:37]([C:46]([F:56])([F:47])[F:48])=[N:36]3)[CH2:23][C:24]3[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=3)=[N:13][C:14]([N:17]([CH2:19][CH2:20][OH:21])[CH3:18])=[CH:15][CH:16]=2)=[C:7]2[C:3]=1[C:4]([NH:51][S:52]([CH3:55])(=[O:53])=[O:54])=[N:5][N:6]2[CH3:50]

Participants

Reactant 2

HCID 90281286(3bS,4aR)-5,5-Difluoro-3b,4,4a,5-tetrahydro-3-(trifluoromethyl)-1H-cyclopropa(3,4)cyclopenta(1,2-c)pyrazole-1-acetic acid

HCID 90281434N-((S)-1-(3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)-6-((2-hydroxyethyl)(methyl)amino)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)-2-((3bS,4aR)-3-(difluoromethyl)-5,5-difluoro-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)acetamide

Product 1

HCID 90290152N-((S)-1-(3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)-6-((2-hydroxyethyl)(methyl)amino)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)-2-((3bS,4aR)-5,5-difluoro-3-(trifluoromethyl)-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)acetamide

Procedure

The title compound (58) was prepared according to the method presented for the synthesis of compound 57G of Example 57 utilizing 2-((3bS,4aR)-5,5-difluoro-3-(trifluoromethyl)-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)acetic acid (30J). 1H NMR (400 MHz, Methanol-d4) δ 7.43-6.05 (m, 7H), 5.18-5.09 (m, 1H), 4.85-4.75 (m 2H), 4.04-3.69 (m, 3H), 3.42 (s, 2H), 3.27-3.20 (m, 6H), 3.20-3.11 (m, 2H), 3.05 (s, 1H), 2.95 (s, 1H), 2.61-2.43 (m, 2H), 1.51-1.35 (m, 1H), 1.11 (m, 1H). MS (m/z) 829.20 [M+H]+.

Sources & evidence

ORD record: ord-f653dd0165c743bbb8aebfa8ba0dca51
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050344B2

Reaction notes

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