Chloroacetamide → HCID 123987634, compound

HRID 1509130Notes

Reaction equation

HRID 1509130 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:20][C:21]4[NH:26][C:25](=[O:27])[CH2:24][O:23][C:22]=4[N:28]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:43][C:44]([NH2:46])=[O:45]>CN(C=O)C>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:19]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:20][C:21]4[N:26]([CH2:43][C:44]([NH2:46])=[O:45])[C:25](=[O:27])[CH2:24][O:23][C:22]=4[N:28]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 67256382HCID 67256382, compound

Product 1

HCID 123987634HCID 123987634, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl(1-(4-(2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (19 mg, 0.04 mmol) in dry DMF (1 mL) was added potassium carbonate (12 mg, 0.08 mmol) and 2-chloroacetamide (12 mg, 0.12 mmol) at room temperature under nitrogen. The reaction mixture was stirred overnight at room temperature and concentrated to dryness under reduced pressure. The resulting residue was purified by silica gel chromatography (gradient 0 to 80% AcOEt in hexane) to give the title compound (14 mg, 67%). 1H NMR (500 MHz, CDCl3): 7.32 (1H, s), 7.28-7.23 (7H,m), 7.16-7.14 (2H,m), 6.22 (1H, br s), 5.65 (1H, br s), 5.09 (1H, br s), 4.94 (2H, s), 4.52 (2H,s), 2.55-2.25 (4H, m), 2.09-2.01 (1H, m), 1.85-1.76 (1H, m), 1.44-1.15 (9H, br).

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. customThe resulting residue was purified by silica gel chromatography (gradient 0 to 80% AcOEt in hexane)

Sources & evidence

ORD record
ord-71d27b15ce82491e90b18a6be399253a
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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