Acetyl chloride → (4-Chloro-2-(1-oxo-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-2(1H)-yl)pyridin-3-yl)methyl acetate

HRID 1411916Notes

Reaction equation

HRID 1411916 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:20][CH2:19][C:18]3[N:17]4[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]4)=[CH:11][C:10]=3[C:9]2=[O:21])[C:3]=1[CH2:22][OH:23].C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>ClCCl>[C:31]([O:23][CH2:22][C:3]1[C:4]([N:8]2[CH2:20][CH2:19][C:18]3[N:17]4[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]4)=[CH:11][C:10]=3[C:9]2=[O:21])=[N:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 866844622-(4-Chloro-3-(hydroxymethyl)pyridin-2-yl)-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-1(2H)-one

Product 1

HCID 86684463(4-Chloro-2-(1-oxo-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-2(1H)-yl)pyridin-3-yl)methyl acetateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To a mixture of 244a (900 mg, 2.7 mmol) and triethylamine (810 mg, 8.1 mmol) in dichloromethane (30 mL) was added acetyl chloride (630 mg, 8.1 mmol) dropwise. The reaction mixture was stirred at 30° C. for 1 h. It was then concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with dichloromethane to afford 244b as white solid (900 mg, 90%). MS-ESI: [M+H]+ 374.2

Workup

  1. concentrationIt was then concentrated under reduced pressure
  2. customthe residue was purified by silica-gel column chromatography
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-afb32023bbcf470eb1b2750d5c5ee8a8
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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