Chloroacetamide → HCID 86605657, compound

HRID 1986484Notes

Reaction equation

HRID 1986484 reaction equation
[CH2:1]([C:5]1[C:14]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[C:13]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:31]3[N:32]=[N:33][NH:34][N:35]=3)[CH:11]=2)[N:6]=1)[CH:2]([CH3:4])[CH3:3].Cl[CH2:37][C:38]([NH2:40])=[O:39].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:40][C:38](=[O:39])[CH2:37][N:33]1[N:34]=[N:35][C:31]([C:10]2[CH:11]=[C:12]3[C:7](=[CH:8][CH:9]=2)[N:6]=[C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:14]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[C:13]3[C:24]2[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=2)=[N:32]1

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 86605653HCID 86605653, compound

Product 1

HCID 86605657HCID 86605657, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl [2-isobutyl-4-(4-methylphenyl)-6-(2H-tetrazol-5-yl)quinolin-3-yl]methylcarbamate (0.16 g, 0.33 mmol), 2-chloroacetamide (0.047 g, 0.50 mmol), potassium carbonate (0.070 g, 0.50 mmol) and N,N-dimethylformamide (5 ml) was stirred at 80° C. for 3 hrs. The reaction mixture was partitioned between ethyl acetate-tetrahydrofuran and water and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined and washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give tert-butyl [6-[2-(2-amino-2-oxoethyl)-2H-tetrazol-5-yl]-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methylcarbamate (0.12 g, yield 69%) as a pale-yellow powder.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate-tetrahydrofuran and water
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washwashed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-774859b7cc94430d96f10a7b4cb4a3ca
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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