Ethyl 1-amino-2-vinylcyclopropanecarboxylate → 2-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-[2-(2-isopropylamino-thiazol-4-yl)-7-methoxy-quinolin-4-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 643829Notes

Reaction equation

HRID 643829 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=3)[N:17]=[C:16]([C:26]3[N:27]=[C:28]([NH:31][CH:32]([CH3:34])[CH3:33])[S:29][CH:30]=3)[CH:15]=2)[CH2:10][CH:9]1[C:35]([OH:37])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:38]([O:40][C:41]([C:43]1([NH2:48])[CH2:45][CH:44]1[CH:46]=[CH2:47])=[O:42])[CH3:39]>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=3)[N:17]=[C:16]([C:26]3[N:27]=[C:28]([NH:31][CH:32]([CH3:33])[CH3:34])[S:29][CH:30]=3)[CH:15]=2)[CH2:10][CH:9]1[C:35](=[O:37])[NH:48][C:43]1([C:41]([O:40][CH2:38][CH3:39])=[O:42])[CH2:45][CH:44]1[CH:46]=[CH2:47])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 22082824Ethyl 1-amino-2-vinylcyclopropanecarboxylateHCID 749555114-[2-(2-Isopropylamino-thiazol-4-yl)-7-methoxy-quinolin-4-yloxy]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Product 1

HCID 207736652-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-[2-(2-isopropylamino-thiazol-4-yl)-7-methoxy-quinolin-4-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl esterYield 81%

Procedure

Compound 21 (300 mg, 0.56 mmol) was reacted with 1-amino-2-vinyl-cyclopropanecarboxylic acid ethyl ester (130 mg, 0.84 mmol) as described in Example 5 which gave the title compound (302 mg, 80%).

Sources & evidence

ORD record
ord-e108b58241044cc9ad4daf8d1a4c8e00
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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