2-(Methylamino)ethanol → HCID 58914772, compound

HRID 1297497Notes

Reaction equation

HRID 1297497 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[C:14]1[C:15]([NH:33][C:34](=[O:37])[CH2:35]Br)=[CH:16][N:17]([CH2:19][CH2:20][CH2:21][N:22]2[C:26](=[O:27])[C:25]3[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=3[C:23]2=[O:32])[CH:18]=1>CC#N>[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[C:14]1[C:15]([NH:33][C:34](=[O:37])[CH2:35][N:2]([CH2:3][CH2:4][OH:5])[CH3:1])=[CH:16][N:17]([CH2:19][CH2:20][CH2:21][N:22]2[C:26](=[O:27])[C:25]3[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=3[C:23]2=[O:32])[CH:18]=1

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 58914804HCID 58914804, compound

Product 1

HCID 58914772HCID 58914772, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Methyl ethanolamine (2 eq) was added to a stirred solution of N-{4-(2,4-dichlorophenyl)-1-[3-(1,3-dioxobenzo[c]azolin-2-yl)propyl]pyrrol-3-yl}-2-bromcacetamide (6) (8.65 eq) in CH3CN at RT. The reaction was monitored by LC/MS and was determined to be complete after 12 hours. The reaction was concentrated and purified by silica column chromatography eluting with MeOH in CH2Cl2 (5:95, v/v). After collecting the purified fractions and concentrating, N-{4-(2,4-dichlorophenyl)-1-[3-(1,3-dioxobenzo[c]azolin-2-yl)propyl]pyrrol-3-yl}-2-[(2-hydroxyethyl)methylamino]acetamide (7) was obtained as a light yellow glass (21% yield, LC/MS m/z 530.4 MH+) in 95% purity.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by silica column chromatography
  3. washeluting with MeOH in CH2Cl2 (5:95
  4. customAfter collecting the purified fractions
  5. concentrationconcentrating

Sources & evidence

ORD record
ord-c6648d709b014b47a7bb25c399911526
Source dataset
uspto-grants-2007_07
Patent number
US07250443B2

Reaction notes

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