Dimethylformamide → HCID 131719827, compound

HRID 1449832Notes

Reaction equation

HRID 1449832 reaction equation
CN(C)[CH:3]=[O:4].[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][O:14][C:15](=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br.[NH2:23][CH2:24][CH:25]([C:27]1[CH:32]=[C:31]([Cl:33])[C:30]([NH2:34])=[C:29]([Cl:35])[CH:28]=1)[OH:26]>C(OCC)(=O)C.CO.C(N(CC)CC)C>[C:3]([OH:4])(=[O:26])/[CH:17]=[CH:16]/[C:15]([OH:14])=[O:22].[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][O:14][C:15](=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:23][CH2:24][CH:25]([C:27]1[CH:28]=[C:29]([Cl:35])[C:30]([NH2:34])=[C:31]([Cl:33])[CH:32]=1)[OH:26].[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][O:14][C:15](=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:23][CH2:24][CH:25]([OH:26])[C:27]1[CH:32]=[C:31]([Cl:33])[C:30]([NH2:34])=[C:29]([Cl:35])[CH:28]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 217242Benzenemethanol, 4-amino-alpha-(aminomethyl)-3,5-dichloro-HCID 54109772HCID 54109772, compound

Product 1

HCID 131719827HCID 131719827, compound

Reagents, catalysts & solvents 1

HCID 21980445Ethyl acetate methanol triethylamineSolvent

Procedure

According to method I (dimethylformamide, 1 hour at 90° C.) from {2-(2-pyridyl)ethyl}6-bromohexanoate and 2-amino-1-(4-amino-3,5-dichlorophenyl)ethanol. Working up by means of chromatography (ethyl acetate/methanol/triethylamine 20:2:1). Recrystallized as the hemifumarate from acetone. Melting point: 75°-76° C.

Workup

  1. customRecrystallized as the hemifumarate from acetone

Sources & evidence

ORD record
ord-dcda4681dff6451bb3b6ce0f25033c33
Source dataset
uspto-grants-1997_02
Patent number
US05599966

Reaction notes

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