N-((S)-1-(5-amino-3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)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 → N-((S)-1-(5-amino-6-chloro-3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)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

HRID 2170390Notes

Reaction equation

HRID 2170390 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:36]2[CH:37]=[CH:38][C:39]([Cl:51])=[C:40]3[C:44]=2[N:43]([CH3:45])[N:42]=[C:41]3[NH:46][S:47]([CH3:50])(=[O:49])=[O:48])[C:5]([C@@H:8]([NH:18][C:19](=[O:35])[CH2:20][N:21]2[C:25]3[C:26]([F:31])([F:30])[C@@H:27]4[CH2:29][C@@H:28]4[C:24]=3[C:23]([CH:32]([F:34])[F:33])=[N:22]2)[CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)=[N:6][CH:7]=1.NC1C=C(C2C=CC([Cl:92])=C3C=2N(C)N=C3NS(C)(=O)=O)C([C@@H](NC(=O)OC(C)(C)C)CC2C=C(F)C=C(F)C=2)=NC=1>>[NH2:1][C:2]1[CH:3]=[C:4]([C:36]2[CH:37]=[CH:38][C:39]([Cl:51])=[C:40]3[C:44]=2[N:43]([CH3:45])[N:42]=[C:41]3[NH:46][S:47]([CH3:50])(=[O:48])=[O:49])[C:5]([C@@H:8]([NH:18][C:19](=[O:35])[CH2:20][N:21]2[C:25]3[C:26]([F:31])([F:30])[C@@H:27]4[CH2:29][C@@H:28]4[C:24]=3[C:23]([CH:32]([F:34])[F:33])=[N:22]2)[CH2:9][C:10]2[CH:11]=[C:12]([F:17])[CH:13]=[C:14]([F:16])[CH:15]=2)=[N:6][C:7]=1[Cl:92]

Participants

3

Reactant 2

HCID 90281283N-((S)-1-(5-amino-3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)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)acetamideHCID 90290153(S)-tert-butyl (1-(5-amino-3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

Product 1

HCID 90281413N-((S)-1-(5-amino-6-chloro-3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)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

Procedure

Compound 53B was prepared according to the method presented for the synthesis of compound 49C in Example 49 substituting 53A for 49A to provide the title compound: 1H NMR (400 MHz, methanol-d4) δ 7.17-6.94 (m, 2H), 6.87-6.54 (m, 2H), 6.53-6.19 (m, 3H), 4.96 (s, 1H), 4.72 (dd, 2H), 3.41 (s, 2H), 3.24 (d, 3H), 3.16-2.88 (m, 3H), 1.38 (dt, 1H), 1.13-0.99 (m, 1H). MS (m/z) 787 [M+H]+.

Workup

  1. customCompound 53B was prepared

Sources & evidence

ORD record
ord-28046370cba94f9581c888e1ff1ad479
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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