Dicyclohexylcarbodiimide → HCID 53683817, compound

HRID 344440Notes

Reaction equation

HRID 344440 reaction equation
[CH2:1]([N:8]([CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH:16]([CH2:19][NH2:20])[CH2:15]1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:21][C:22]1[C:30]([Cl:31])=[CH:29][C:25]([C:26](O)=[O:27])=[C:24]([O:32][CH3:33])[CH:23]=1.C1(N=C=NC2CCCCC2)CCCCC1.ON1N=C2C=CC=CC2=N1>CN(C)C=O.C(N(CC)CC)C>[NH2:21][C:22]1[C:30]([Cl:31])=[CH:29][C:25]([C:26]([NH:20][CH2:19][CH:16]2[CH2:17][CH2:18][N:14]([CH2:13][CH2:12][CH2:11][CH2:10][N:8]([CH3:9])[CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:15]2)=[O:27])=[C:24]([O:32][CH3:33])[CH:23]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 15905956HCID 15905956, compoundHCID 54552954HCID 54552954, compound

Product 1

HCID 53683817HCID 53683817, compoundYield 10.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of N-benzyl-N-methyl-4-(3-aminomethylpyrrolidin-1-yl)-butylamine (1.06 g), 4-amino-5-chloro-2-methoxybenzoic acid (0.78 g), dicyclohexylcarbodiimide (0.79 g), 2-hydroxybenzotriazole (0.52 g) and triethylamine (1.1 ml) in N,N-dimethylformamide (20 ml) was stirred at room temperature for 12 hr. The solvent was evaporated, and water was added to the residue, which was followed by extraction with chloroform. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 0.19 g of 4-amino-5-chloro-2-methoxy-N-((1-(4-(N-methyl-N-benzylamino)butyl)pyrrolidin-3-yl)methyl)-benzamide.

Workup

  1. customThe solvent was evaporated
  2. additionwater was added to the residue, which
  3. extractionwas followed by extraction with chloroform
  4. washThe organic layer was washed with brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b7be9c27bbcd4c9bbdfcc55e2a7645b4
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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