Trifluoroacetic acid → methyl 4-[({1-[(2-methyl-4-quinolinyl)methyl]-1H-indol-5-yl}carbonyl)amino]-3-pyrrolidinecarboxylate

HRID 351967Notes

Reaction equation

HRID 351967 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][C:9]1[CH:18]=[C:17]([CH2:19][N:20]2[C:28]3[C:23](=[CH:24][C:25]([C:29]([NH:31][CH:32]4[CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH:33]4[C:44]([O:46][CH3:47])=[O:45])=[O:30])=[CH:26][CH:27]=3)[CH:22]=[CH:21]2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1>C(Cl)Cl>[CH3:8][C:9]1[CH:18]=[C:17]([CH2:19][N:20]2[C:28]3[C:23](=[CH:24][C:25]([C:29]([NH:31][CH:32]4[CH2:36][NH:35][CH2:34][CH:33]4[C:44]([O:46][CH3:47])=[O:45])=[O:30])=[CH:26][CH:27]=3)[CH:22]=[CH:21]2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 222584971-tert-butyl 3-methyl 4-[({1-[(2-methyl-4-quinolinyl)methyl]-1H-indol-5-yl}carbonyl)amino]-1,3-pyrrolidinedicarboxylate

Product 1

HCID 22258348methyl 4-[({1-[(2-methyl-4-quinolinyl)methyl]-1H-indol-5-yl}carbonyl)amino]-3-pyrrolidinecarboxylateYield 186.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2mL) was added to a solution of the coupled product (0.11 g, 0.2 mmol) from step (501c) in methylene chloride (3 mL) at room temperature. The reaction was complete after stirring for 2 h and was concentrated to give methyl 4-[({1-[(2-methyl-4-quinolinyl)methyl]-1H-indol-5-yl}carbonyl)amino]-3-pyrrolidinecarboxylate (0.165 g, 100%) as an oil, MS (M+2H)++=222.

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-f620b2d58ad24c4fa77ebc43727d2213
Source dataset
uspto-grants-2004_06
Patent number
US06743807B2

Reaction notes

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