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

HRID 2170354Notes

Reaction equation

HRID 2170354 reaction equation
[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C@@H:15]([NH:25][C:26](=[O:44])[CH2:27][N:28]3[C:36]4[C:35]([F:38])([F:37])[CH2:34][CH2:33][C:32]([F:40])([F:39])[C:31]=4[C:30]([CH:41]([F:43])[F:42])=[N:29]3)[CH2:16][C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=3)[C:12]([C:45]3[CH:46]=[CH:47][C:48]([F:54])=[C:49]([CH:53]=3)[C:50]([NH2:52])=[O:51])=[CH:11][N:10]=2)[CH:5]=[CH:4]N=N1.N1(CCN)CC[CH2:57][CH2:56]1.BrC1C([C@@H](NC(=O)OC(C)(C)C)CC2C=C(F)C=C(F)C=2)=NC(S(C)(=O)=O)=NC=1>>[F:42][CH:41]([F:43])[C:30]1[C:31]2[C:32]([F:39])([F:40])[CH2:33][CH2:34][C:35]([F:38])([F:37])[C:36]=2[N:28]([CH2:27][C:26]([NH:25][C@H:15]([C:13]2[C:12]([C:45]3[CH:46]=[CH:47][C:48]([F:54])=[C:49]([CH:53]=3)[C:50]([NH2:52])=[O:51])=[CH:11][N:10]=[C:9]([NH:8][CH2:7][CH2:6][N:1]3[CH2:57][CH2:56][CH2:4][CH2:5]3)[N:14]=2)[CH2:16][C:17]2[CH:18]=[C:19]([F:24])[CH:20]=[C:21]([F:23])[CH:22]=2)=[O:44])[N:29]=1

Participants

4

Reactant 3

HCID 13441-PyrrolidineethanamineHCID 90281460(S)-5-(2-((2-(1H-1,2,3-triazol-1-yl)ethyl)amino)-4-(1-(2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamido)-2-(3,5-difluorophenyl)ethyl)pyrimidin-5-yl)-2-fluorobenzamideHCID 90290216(S)-tert-butyl (1-(5-bromo-2-(methylsulfonyl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

Product 1

HCID 90312241(S)-5-(4-(1-(2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamido)-2-(3,5-difluorophenyl)ethyl)-2-((2-(pyrrolidin-1-yl)ethyl)amino)pyrimidin-5-yl)-2-fluorobenzamide

Procedure

The title compound (27) was prepared according to the method presented for the synthesis of compound 23F of Example 23 starting with 2-(pyrrolidin-1-yl)ethanamine and 23B. 1H NMR (400 MHz, CD3OD) δ 8.67 (d, J=7.8 Hz, 1H), 8.05 (s, 1H), 7.41-7.23 (m, 2H), 7.13 (dd, J=10.7, 8.5 Hz, 1H), 6.95-6.48 (m, 2H), 6.35 (d, J=6.2 Hz, 2H), 5.15 (m, 1H), 4.95 (q, J=16.7 Hz, 2H), 3.74 (m, 4H), 3.43 (m, 2H), 3.11 (m, 2H), 3.00-2.88 (m, 2H), 2.70-2.28 (m, 4H), 2.13-1.89 (m, 4H). MS (m/z) 769.29 [M+H]+.

Sources & evidence

ORD record
ord-2d16693de1c34c82b2a6f2c7428dc2f5
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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