1,3-Dichloroacetone → HCID 90271915, compound

HRID 1503892Notes

Reaction equation

HRID 1503892 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[CH:13][C:12]=2[O:30][CH3:31])[C:3]=1[C:32](=[O:34])[NH2:33].[Cl:35][CH2:36][C:37](=O)[CH2:38]Cl>O(CCOC)C>[C:32]([C:3]1[C:2]2[N:7]([CH:38]=[C:37]([CH2:36][Cl:35])[N:1]=2)[C:6]([S:8][CH3:9])=[N:5][C:4]=1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[CH2:19][CH2:18]2)=[CH:13][C:12]=1[O:30][CH3:31])(=[O:34])[NH2:33]

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 90272088HCID 90272088, compound

Product 1

HCID 90271915HCID 90271915, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the product of Example 13D (629 mg, 1.28 mmol) and 1,3-dichloropropan-2-one (652 mg, 5.13 mmol) in 1,2-dimethoxylethane (20 mL) was heated at 80° C. for 18 hours. The mixture was concentrated and the residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 97/3 dichloromethane/methanol to give the title compound. MS: 562 (M+H+).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash chromatography on silica gel (200-300 mesh)
  3. washeluting with 97/3 dichloromethane/methanol

Sources & evidence

ORD record
ord-5ebfd2fa545c4e28a95b7387a5c8ef91
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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