Diisopropylamine → HCID 54473678, compound

HRID 1857637Notes

Reaction equation

HRID 1857637 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:31])=[C:24]([CH2:27][C:28]([OH:30])=O)[CH:25]=2)[NH:20][C:19](=[O:32])[C:18]=1[C:33]1[CH:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[CH:34]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:41]([NH:44][CH:45]([CH3:47])[CH3:46])([CH3:43])[CH3:42].Cl.CN(C)CCCN=C=NCC.CN(C1C=CC=CN=1)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:31])=[C:24]([CH2:27][C:28](=[O:30])[N:44]([CH:45]([CH3:47])[CH3:46])[CH:41]([CH3:43])[CH3:42])[CH:25]=2)[NH:20][C:19](=[O:32])[C:18]=1[C:33]1[CH:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[CH:34]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54398908HCID 54398908, compound

Product 1

HCID 54473678HCID 54473678, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{2-[6-carboxymethyl-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (57 mg in 0.50 mL methylene chloride) was added 0.042 mL diisopropylamine followed by 98 mg 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) and 6.1 mg dimethylaminopyridine, and the mixture stirred at room temperature. After 42 hours, the mixture was diluted with methylene chloride and washed with water and brine. The organics were dried over sodium sulfate and the concentrate purified by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 97:2:1) to give the title compound (41 mg).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organics were dried over sodium sulfate
  3. customthe concentrate purified by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 97:2:1)

Sources & evidence

ORD record
ord-22de1b0f7f9e4664ac7db9d7af353b79
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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