Acetyl chloride → HCID 66701094, compound

HRID 2075516Notes

Reaction equation

HRID 2075516 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[C:5]([NH:9][C:10]([C:12]1[CH:21]=[C:20]([Cl:22])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[O:23][CH2:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:11])([CH3:8])[CH2:6][CH3:7])[CH3:2].[C:32](Cl)(=[O:34])[CH3:33].CCN(CC)CC>ClCCl>[CH2:1]([O:3][C:4](=[O:31])[C:5]([NH:9][C:10]([C:12]1[CH:21]=[C:20]([Cl:22])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[O:23][CH2:24][CH:25]1[CH2:26][CH2:27][N:28]([C:32](=[O:34])[CH3:33])[CH2:29][CH2:30]1)=[O:11])([CH3:8])[CH2:6][CH3:7])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 66701077HCID 66701077, compound

Product 1

HCID 66701094HCID 66701094, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 70 mg of 2-{[4-chloro-1-(piperidin-4-yl-methoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-butyric acid ethyl ester in 4 mL dichloromethane was added 0.026 ml of acetyl chloride followed by addition of 0.13 mL Et3N. This mixture was stirred overnight. The mixture was concentrated and chromatographed on silica with 7 N NH3 in MeOH/dichloromethane to give 76 mg of 2-{[1-(1-acetyl-piperidin-4-ylmethoxy)-4-chloro-naphthalene-2-carbonyl]-amino}-2-methyl-butyric acid ethyl ester.

Workup

  1. concentrationThe mixture was concentrated
  2. customchromatographed on silica with 7 N NH3 in MeOH/dichloromethane

Sources & evidence

ORD record
ord-2a02c9c1f93d477ab0fb589921344383
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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