4-tert-Butylbenzaldehyde → HCID 86603114, compound

HRID 855430Notes

Reaction equation

HRID 855430 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]([CH3:24])[CH2:21][CH2:22][NH2:23])=[CH:16][CH:15]=1.[BH4-].[Na+].[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][C:34]=2[C:36](O)=[O:37])[CH:29]=[CH:28]1.CCN=C=NCCCN(C)C.Cl>CO>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][N:23]([CH2:22][CH2:21][N:20]([C:17]2[CH:16]=[CH:15][C:14]([Cl:13])=[CH:19][CH:18]=2)[CH3:24])[C:36]([C:34]2[CH:33]=[CH:32][CH:31]=[C:30]3[C:35]=2[NH:27][CH:28]=[CH:29]3)=[O:37])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 703244-tert-ButylbenzaldehydeHCID 742811H-Indole-7-carboxylic acidHCID 88988N-(4-Chlorophenyl)-N-methylethylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 86603114HCID 86603114, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

81 mg (0.5 mmol) of 4-tert-butyl benzaldehyde and 92 mg (0.5 mmol) of N-(4-chloro-phenyl)-N-methyl-ethane-1,2-diamine were dissolved in 2 ml methanol and the solution was stirred for 2 h at rt. 18.5 mg (0.5 mmol) of sodium borohydride were added in portions under nitrogen. The reaction mixture was stirred at rt for 30 min, the solvent was evaporated and the residue was suspended in 4 ml DCM. 88 mg (0.55 mol) of 1H-indole-7-carboxylic acid and 105 mg (0.55 mmol) of EDC.HCl were added and the mixture was stirred at rt over night. The product was purified by column chromatography (silica gel, diethyl ether) to yield 140 mg (59%) product as a colorless oil. MS (ISP) 474.4 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at rt for 30 min
  2. customthe solvent was evaporated
  3. stirringthe mixture was stirred at rt over night
  4. customThe product was purified by column chromatography (silica gel, diethyl ether)

Sources & evidence

ORD record
ord-3b3fd4fb26444835a236ffb533003970
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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