Acetic Anhydride → 1-{6-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-pyrrolidin-1-ylmethyl-3,4-dihydro-2H-quinolin-1-yl}-ethanone

HRID 271710Notes

Reaction equation

HRID 271710 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]#[C:22][C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[NH:29][CH:28]([CH2:33][N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[CH2:27][CH2:26]4)=[N:19][CH:20]=2)=[CH:11][CH:10]=1>C(Cl)Cl>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]#[C:22][C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[N:29]([C:5](=[O:7])[CH3:6])[CH:28]([CH2:33][N:34]3[CH2:35][CH2:36][CH2:37][CH2:38]3)[CH2:27][CH2:26]4)=[N:19][CH:20]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7918Acetic Anhydride2×HCID 117432956-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-2-pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydro-quinoline

Product 1

HCID 598358431-{6-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-pyrrolidin-1-ylmethyl-3,4-dihydro-2H-quinolin-1-yl}-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

74 μL (0.77 mmol) acetic anhydride are added to a solution of 220 mg (0.51 mmol) 6-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydro-quinoline (see Example 3.46) in 5 mL DCM and the mixture is stirred for 2 h at RT. Another 0.37 mL (3.85 mmol) acetic anhydride are added and the reaction is stirred for a further 4 days at RT. The solvent is eliminated i.vac. The purification is carried out by column chromatography using HPLC-MS.

Workup

  1. stirringthe reaction is stirred for a further 4 days at RT
  2. customThe purification

Sources & evidence

ORD record
ord-83aaa1bc9c4a43bab0afdb3ef5f5601c
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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