Dimethylformamide → HCID 86605660, compound

HRID 1986493Notes

Reaction equation

HRID 1986493 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([CH2:35][CH:36]([CH3:38])[CH3:37])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[CH:17][C:16]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32](O)=[O:33])=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C([N:42]=C=NCCCN(C)C)C.[NH4+].ON1C2C=CC=CC=2N=N1.CN(C)C=O>O>[NH2:42][C:32](=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28][O:27][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:10]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[C:19]2[C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 68828932HCID 68828932, compound

Product 1

HCID 86605660HCID 86605660, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-{[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}pentanoic acid (0.8 g, 1.5 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.38 g, 2.0 mmol), 1-hydroxy-1H-benzotriazole ammonium salt (0.24 g, 1.6 mmol) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 15 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate, 1N hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from isopropyl ether to give tert-butyl {{6-[(5-amino-5-oxopentyl)oxy]-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl}methyl}carbamate (0.6 g, yield 77%) as crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with saturated aqueous sodium hydrogen carbonate, 1N hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-7d29799353244bea86e9d18fa31d7f75
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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