Pyrrolidine → HCID 59190194, compound

HRID 1645269Notes

Reaction equation

HRID 1645269 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[O:14][C:15](/[CH:18]=[C:19]3/[C:20](=[O:28])[NH:21][C:22]4[C:27]/3=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:16][CH:17]=2)[CH:8]=1)=[O:5].[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>CN1C(=O)CCC1>[O:28]=[C:20]1[NH:21][C:22]2[C:27](/[C:19]/1=[CH:18]\[C:15]1[O:14][C:13]([C:9]3[CH:8]=[C:7]([NH:6][C:4](=[O:5])[CH2:3][CH2:2][N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)[CH:12]=[CH:11][CH:10]=3)=[CH:17][CH:16]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 59190271HCID 59190271, compound

Product 1

HCID 59190194HCID 59190194, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of (E)-3-chloro-N-(3-(5-((2-oxoindolin-3-ylidene)methyl)furan-2-yl)phenyl)propanamide (25 mg, 0.06 mmol) and pyrrolidine (0.025 mL) in NMP (0.75 mL) was heated in microwave (100° C., 5 min). The reaction mixture was purified by RHPLC to yield the desired (E)-N-(3-(5-((2-oxoindolin-3-ylidene)methyl)furan-2-yl)phenyl)-3-(pyrrolidin-1-yl)propanamide LCMS (ES): m/z 428 [M+1]+.

Workup

  1. customThe reaction mixture was purified by RHPLC

Sources & evidence

ORD record
ord-6fd3283562ad4514969a06c352d2f370
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Reaction notes

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