Dicyclohexylcarbodiimide → HCID 22917141, compound

HRID 1376508Notes

Reaction equation

HRID 1376508 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12](O)=[O:13])[C:6]=2[O:5][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:3]1.ON1C2C=CC=CC=2N=N1.[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][C:42]=1[O:43][CH3:44])[CH2:39][N:38]([CH2:45][CH2:46][CH2:47][CH2:48][C:49]1[CH:54]=[CH:53][C:52]([NH2:55])=[CH:51][CH:50]=1)[CH2:37][CH2:36]2.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][C:42]=1[O:43][CH3:44])[CH2:39][N:38]([CH2:45][CH2:46][CH2:47][CH2:48][C:49]1[CH:54]=[CH:53][C:52]([NH:55][C:12]([C:11]3[C:6]4[O:5][C:4]([C:15]5[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=5)=[CH:3][C:2](=[O:1])[C:7]=4[CH:8]=[CH:9][CH:10]=3)=[O:13])=[CH:51][CH:50]=1)[CH2:37][CH2:36]2

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 12407955HCID 12407955, compoundHCID 22917132HCID 22917132, compound2×

Product 1

HCID 22917141HCID 22917141, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylic acid* (1 g) and 1-hydroxybenzotriazole (0.58 g) in DMF (50 ml) was stirred at room temperature for 10 min. 4-[4-(1,2,3,4-Tetrahydro-6,7-dimethoxy-2-isoquinolinyl)butyl]benzenamine (intermediate 2(d) in EP-A-494623) (1.1 g) was then added, followed by dicyclohexylcarbodiimide (0.67 g) and the mixture was stirred at room temperature for 16 h and then filtered. The filtrate was concentrated in vacuo, treated with dilute sodium hydroxide solution and extracted with methylene chloride. The combined, dried, organic extracts were evaporated and the residue was purified by column chromatography on silica gel eluting with methylene chloride/methanol (99:1) to give the title compound (0.6 g) as a white solid, after crystallisation from ethyl acetate, mp=117°-120°.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. additiontreated with dilute sodium hydroxide solution
  5. extractionextracted with methylene chloride
  6. customdried
  7. customorganic extracts were evaporated
  8. customthe residue was purified by column chromatography on silica gel eluting with methylene chloride/methanol (99:1)

Sources & evidence

ORD record
ord-e0686b4963db474caed653b78d59e04a
Source dataset
uspto-grants-1997_09
Patent number
US05663179

Reaction notes

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