Cyclopropylamine → (2S,4S)-4-(8-chloro-7-methoxy-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)quinolin-4-yloxy)-N1-((1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropyl)-N2-(hex-5-enyl)-N2-methylpyrrolidine-1,2-dicarboxamide

HRID 420080Notes

Reaction equation

HRID 420080 reaction equation
[Cl:1][C:2]1[C:3]([O:48][CH3:49])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([N:12]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[N:13]1)[CH:8]=[C:7]2[O:21][C@@H:22]1[CH2:26][N:25]([C:27]([NH:29][C@:30]2(C(O)=O)[CH2:32][C@H:31]2[CH:33]=[CH2:34])=[O:28])[C@H:24]([C:38](=[O:47])[N:39]([CH2:41][CH2:42][CH2:43][CH2:44][CH:45]=[CH2:46])[CH3:40])[CH2:23]1.C1(N)CC1.[C:54](=[N:56][S:57]([C:60]1(C)[CH2:62][CH2:61]1)(=[O:59])=[O:58])=[O:55]>>[Cl:1][C:2]1[C:3]([O:48][CH3:49])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([N:12]1[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:20])[F:18])=[N:13]1)[CH:8]=[C:7]2[O:21][C@@H:22]1[CH2:26][N:25]([C:27]([NH:29][C@:30]2([C:54](=[O:55])[NH:56][S:57]([CH:60]3[CH2:62][CH2:61]3)(=[O:59])=[O:58])[CH2:32][C@H:31]2[CH:33]=[CH2:34])=[O:28])[C@H:24]([C:38]([N:39]([CH2:41][CH2:42][CH2:43][CH2:44][CH:45]=[CH2:46])[CH3:40])=[O:47])[CH2:23]1

Participants

4

Reactant 3

HCID 69828CyclopropylamineHCID 57816664(1R,2S)-1-((2S,4S)-4-(8-chloro-7-methoxy-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)quinolin-4-yloxy)-2-(hex-5-enyl(methyl)carbamoyl)pyrrolidine-1-carboxamido)-2-vinylcyclopropanecarboxylic acidHCID 86633209Carbonyl(1-methyl-cyclopropyl)sulfonamide

Product 1

HCID 57816701(2S,4S)-4-(8-chloro-7-methoxy-2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)quinolin-4-yloxy)-N1-((1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropyl)-N2-(hex-5-enyl)-N2-methylpyrrolidine-1,2-dicarboxamideYield 40%

Procedure

Compound 118 was synthesized from compound 117 and cyclopropylamine as a white solid in 40% yield, following the procedure as described for compound 56c.

Sources & evidence

ORD record
ord-8a09aaa1d96b48b69fe8bf7368470d2f
Source dataset
uspto-grants-2012_01
Patent number
US08093379B2

Reaction notes

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