1-(2-Aminoethyl)pyrrolidin-2-one → (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-(2-oxopyrrolidin-1-yl)ethyl)amino)pyrimidin-5-yl)-2-fluorobenzamide

HRID 2170351Notes

Reaction equation

HRID 2170351 reaction equation
N1(CCN[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)C=CN=N1.[NH2:55][CH2:56][CH2:57][N:58]1[CH2:62][CH2:61][CH2:60][C:59]1=[O:63].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:43][CH:41]([F:42])[C:30]1[C:31]2[C:32]([F:39])([F:40])[CH2:33][CH2:34][C:35]([F:37])([F:38])[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:55][CH2:56][CH2:57][N:58]3[CH2:62][CH2:61][CH2:60][C:59]3=[O:63])[N:14]=2)[CH2:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=2)=[O:44])[N:29]=1

Participants

4

Reactant 3

HCID 906601-(2-Aminoethyl)pyrrolidin-2-oneHCID 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 90290148(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-(2-oxopyrrolidin-1-yl)ethyl)amino)pyrimidin-5-yl)-2-fluorobenzamide

Procedure

The title compound (24) was prepared according to the method presented for the synthesis of compound 23F of Example 23 starting with 1-(2-aminoethyl)pyrrolidin-2-one and 23B. MS (m/z) 1H NMR (400 MHz, CD3OD) δ 8.84 (m, 1H), 8.07 (s, 1H), 7.50-7.27 (m, 2H), 7.24-7.11 (m, 1H), 6.97-6.61 (m, 2H), 6.45 (d, J=6.2 Hz, 2H), 5.27 (m, 1H), 5.10 (s, 2H), 3.57 (m, 6H), 3.18-2.87 (m, 2H), 2.51 (m, 4H), 2.41-2.28 (m, 2H), 2.12-1.89 (m, 2H). 783.12 [M+H]+.

Sources & evidence

ORD record
ord-c8c7b692ac214fd7b362a1cf0968b53d
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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