Nitrourea → HCID 72303785, compound

HRID 450800Notes

Reaction equation

HRID 450800 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[N:8]1[CH:17]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[CH:16]([C:26]([NH:28][O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:27])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:37].[N+]([NH:41][C:42](N)=[O:43])([O-])=O>C(O)C>[CH2:30]([O:29][NH:28][C:26]([CH:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:37])[N:8]([CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]2[NH:1][C:42](=[O:43])[NH2:41])[CH:17]1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])=[O:27])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 62372NitroureaHCID 72303218HCID 72303218, compound

Product 1

HCID 72303785HCID 72303785, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixed liquid of 269 mg of (3RS,4RS)-2-[(1SR,2SR)-2-aminocyclohexyl]-N-(benzyloxy)-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-54ad5e7ca7b64d3297433163f5cb00c7
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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