2-(Methylamino)ethanol → HCID 22254156, compound

HRID 1611712Notes

Reaction equation

HRID 1611712 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[NH2:6][C:7]1[N:12]=[C:11]([NH:13][CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:27])[CH2:25]Br)=[C:19]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[Cl:35])[CH:18]=2)[CH:10]=[CH:9][C:8]=1[N+:36]([O-:38])=[O:37]>CC#N>[NH2:6][C:7]1[N:12]=[C:11]([NH:13][CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:27])[CH2:25][N:2]([CH2:3][CH2:4][OH:5])[CH3:1])=[C:19]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[Cl:35])[CH:18]=2)[CH:10]=[CH:9][C:8]=1[N+:36]([O-:38])=[O:37]

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 22254164HCID 22254164, compound

Product 1

HCID 22254156HCID 22254156, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Methyl ethanolamine (2 eq) was added to a stirred solution N-[4-({2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}amino)-2-(2,4-dichlorophenyl)phenyl]-2-bromoacetamide (8.65 eq) in CH3CN at room temperature. 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-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}amino)-2-(2,4-dichlorophenyl)phenyl]-2-[(2-hydroxyethyl)methylamino]acetamide was obtained as a light yellow glass (21% yield, LC/MS m/z 549.4 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-742a2b4a10454e1badd8f4d1f7bf5d27
Source dataset
uspto-grants-2006_01
Patent number
US06989382B2

Reaction notes

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