1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 86603131, compound

HRID 855451Notes

Reaction equation

HRID 855451 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:12]([OH:14])=O)[C:10]=1[F:11])[NH:7][CH:6]=[CH:5]2.[C:15]([C:19]1[CH:35]=[CH:34][C:22]([CH2:23][NH:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:15]([C:19]1[CH:35]=[CH:34][C:22]([CH2:23][N:24]([CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=2)[C:12]([C:9]2[C:10]([F:11])=[C:2]([F:1])[CH:3]=[C:4]3[C:8]=2[NH:7][CH:6]=[CH:5]3)=[O:14])=[CH:21][CH:20]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68564049HCID 68564049, compoundHCID 693460795,6-difluoro-1H-indole-7-carboxylic acid

Product 1

HCID 86603131HCID 86603131, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

87 mg (0.44 mol) of 5,6-difluoro-1H-indol-7-carboxylic acid, 113 mg (0.40 mmol) of (4-tert-butyl-benzyl)-[2-(4-methyl-phenyl)-ethyl]-amine and 84 mg (0.44 mmol) of EDC.HCl were dissolved in 4 ml DCM. The reaction mixture was stirred at rt over night. The solvent was evaporated and the residue was purified by column chromatography (20 g silica gel; heptane/EtOAc 4:1) to yield 69 mg (38%) product as a colorless viscous oil. MS (ISP) 461.3 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography (20 g silica gel; heptane/EtOAc 4:1)

Sources & evidence

ORD record
ord-a66bdfd03c3b4ad69f5f5ca192ad052d
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

Loading…