(S)-5-(2-(1-(2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamido)-2-(3,5-difluorophenyl)ethyl)-5-(1,3-dioxoisoindolin-2-yl)pyridin-3-yl)-2-fluorobenzamide → (S)-5-(5-amino-2-(1-(2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamido)-2-(3,5-difluorophenyl)ethyl)pyridin-3-yl)-2-fluorobenzamide

HRID 2170366Notes

Reaction equation

HRID 2170366 reaction equation
[F:1][CH:2]([F:57])[C:3]1[C:11]2[C:10]([F:13])([F:12])[CH2:9][CH2:8][C:7]([F:15])([F:14])[C:6]=2[N:5]([CH2:16][C:17]([NH:19][C@H:20]([C:30]2[C:35]([C:36]3[CH:37]=[CH:38][C:39]([F:45])=[C:40]([CH:44]=3)[C:41]([NH2:43])=[O:42])=[CH:34][C:33]([N:46]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:32][N:31]=2)[CH2:21][C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[CH:23]=2)=[O:18])[N:4]=1.FC1(F)C2N(CC(N[C@H](C3C(C4C=CC(F)=C(C=4)C(N)=O)=CC(N4C(=O)C5C(=CC=CC=5)C4=O)=CN=3)CC3C=C(F)C=C(F)C=3)=O)N=C(C(F)(F)F)C=2[C@H]2C[C@@H]12>>[NH2:46][C:33]1[CH:34]=[C:35]([C:36]2[CH:37]=[CH:38][C:39]([F:45])=[C:40]([CH:44]=2)[C:41]([NH2:43])=[O:42])[C:30]([C@@H:20]([NH:19][C:17](=[O:18])[CH2:16][N:5]2[C:6]3[C:7]([F:14])([F:15])[CH2:8][CH2:9][C:10]([F:12])([F:13])[C:11]=3[C:3]([CH:2]([F:1])[F:57])=[N:4]2)[CH2:21][C:22]2[CH:23]=[C:24]([F:29])[CH:25]=[C:26]([F:28])[CH:27]=2)=[N:31][CH:32]=1

Participants

3

Reactant 2

HCID 90281315(S)-5-(2-(1-(2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamido)-2-(3,5-difluorophenyl)ethyl)-5-(1,3-dioxoisoindolin-2-yl)pyridin-3-yl)-2-fluorobenzamideHCID 902814515-(2-((S)-1-(2-((3bS,4aR)-5,5-difluoro-3-(trifluoromethyl)-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)acetamido)-2-(3,5-difluorophenyl)ethyl)-5-(1,3-dioxoisoindolin-2-yl)pyridin-3-yl)-2-fluorobenzamide

Product 1

HCID 90281328(S)-5-(5-amino-2-(1-(2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamido)-2-(3,5-difluorophenyl)ethyl)pyridin-3-yl)-2-fluorobenzamide

Procedure

Compound 33 was prepared according to the method presented in the synthesis of Example 31 substituting compound 32 for compound 30K. 1H NMR (400 MHz, CD3OD) δ 8.08 (d, 1H), 7.39 (m, 2H), 7.28-7.17 (m, 1H), 7.14 (d, 1H), 7.00-6.60 (m, 2H), 6.37 (m, 2H), 5.19-5.01 (m, 3H), 3.12 (m, 1H), 2.99 (m, 1H), 2.66-2.34 (m, 4H). MS (m/z) 671.01 [M+H]+.

Sources & evidence

ORD record
ord-576dad1c21f041b19d4fdad8a1e4c384
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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