Nitrourea → HCID 72303785, compound

HRID 1747076Notes

Reaction equation

HRID 1747076 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH:18]([C:19]([NH2:21])=[O:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:22])[NH:10]1.[N+]([NH:26][C:27]([NH2:29])=[O:28])([O-])=O>C(O)C>[CH2:11]([O:22][NH:21][C:19]([CH:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:22])[N:10]([CH:3]2[CH2:2][CH2:7][CH2:6][CH2:5][CH:4]2[NH:26][C:27](=[O:28])[NH2:29])[CH:9]1[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 62372NitroureaHCID 131733554HCID 131733554, compound

Product 1

HCID 72303785HCID 72303785, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixed liquid of 269 mg of (3RS,4RS)-2-[(1SR,2SR)-2-aminocyclohexyl]-Nenzyloxy)-3-(2,4-dichlorophenyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide and 20 ml of ethanol was added 53 mg of nitrourea, followed by heating under reflux for 1 hour. The reaction solution was cooled and then concentrated, and the residue was purified by silica gel column chromatography (eluent:chloroform-methanol), then crystallized with acetonitrile, and collected by filtration to obtain 155 mg of (3RS,4RS)—N-(benzyloxy)-2-[(1SR,2SR)-2-(carbamoylamino)cyclohexyl]-3-(2,4-dichlorophenyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide as a white crystal.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1 hour
  3. temperatureThe reaction solution was cooled
  4. concentrationconcentrated
  5. customthe residue was purified by silica gel column chromatography (eluent:chloroform-methanol)
  6. customcrystallized with acetonitrile
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-d0667c955a7a4187b9d3af75a6528c93
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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