O-Methylisourea → HCID 178492692, compound

HRID 1005607Notes

Reaction equation

HRID 1005607 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:50]=[CH:49][CH:48]=[CH:47][C:7]=1[C:8]([NH:10][C:11]1[CH:44]=[CH:43][C:14]([C:15]([N:17]([CH3:42])[C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=2[O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([N:33]2[CH2:38][CH2:37][CH:36]([N:39]([CH3:41])[CH3:40])[CH2:35][CH2:34]2)=[O:32])=[O:16])=[CH:13][C:12]=1[O:45][CH3:46])=[O:9].CO[C:53](=[NH:55])[NH2:54]>C(O)C>[NH:1]([CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:50]=[CH:49][CH:48]=[CH:47][C:7]=1[C:8]([NH:10][C:11]1[CH:44]=[CH:43][C:14]([C:15]([N:17]([CH3:42])[C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=2[O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([N:33]2[CH2:38][CH2:37][CH:36]([N:39]([CH3:40])[CH3:41])[CH2:35][CH2:34]2)=[O:32])=[O:16])=[CH:13][C:12]=1[O:45][CH3:46])=[O:9])[C:53]([NH2:55])=[NH:54]

Participants

4

Reactant 2

HCID 75544O-MethylisoureaHCID 18791394HCID 18791394, compound

Product 1

HCID 178492692HCID 178492692, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[2-(3-aminoprop-1-yl)oxybenzoyl]amino-3-methoxy-N-methyl-N-[2-[5-(4-dimethylaminopiperidin-1-yl)carbonylpent-1-yl]oxy-4-methylphenyl]benzamide (275 mg) and O-methylisourea (44 mg) in ethanol (5 ml) was refluxed for 3 days. The solvent was evaporated in vacuo and the residue was purified on basic silica gel column chromatography (SiO2 17 g, 1-80% methanol in chloroform) to give 4-[2-(3-guanidinoprop-1-yl)oxybenzoyl]amino-3-methoxy-N-methyl-N-[2-[5-(4-dimethylaminopiperidin-1-yl)carbonylpent-1-yl]oxy-4-methylphenyl]benzamide (53 mg).

Workup

  1. temperaturewas refluxed for 3 days
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified on basic silica gel column chromatography (SiO2 17 g, 1-80% methanol in chloroform)

Sources & evidence

ORD record
ord-d50729b788ba46ada875a63031388a8c
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

Loading…