Dichloromethane → (4-Chloro-2-(10-fluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)pyridin-3-yl)methyl Acetate

HRID 592938Notes

Reaction equation

HRID 592938 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:21][CH2:20][N:11]3[C:12]4[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=4[C:18]([F:19])=[C:10]3[C:9]2=[O:22])[C:3]=1[CH2:23][OH:24].ClCCl.[C:28](Cl)(=[O:30])[CH3:29]>C(N(CC)CC)C>[C:28]([O:24][CH2:23][C:3]1[C:4]([N:8]2[CH2:21][CH2:20][N:11]3[C:12]4[CH2:13][CH2:14][CH2:15][CH2:16][C:17]=4[C:18]([F:19])=[C:10]3[C:9]2=[O:22])=[N:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 866844322-(4-Chloro-3-(hydroxymethyl)pyridin-2-yl)-10-fluoro-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one

Product 1

HCID 86684433(4-Chloro-2-(10-fluoro-1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)pyridin-3-yl)methyl AcetateYield 90%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

A round-bottomed flask was charged with 231a (600 mg, 1.72 mmol), dichloromethane (50 mL), and triethylamine (5 mL). The solution was stirred at 0° C. for 0.5 h and acetyl chloride (135 mg, 1.72 mmol) was added slowly. The mixture was stirred at 0° C. for another 2.5 h. It was then evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 9:1 petroleum ether/ethyl acetate to afford 231b (605 mg, 90%) as a yellow solid. MS-ESI: [M+H]+ 392.1

Workup

  1. stirringThe mixture was stirred at 0° C. for another 2.5 h
  2. customIt was then evaporated under reduced pressure
  3. customThe residue was purified by silica-gel column chromatography
  4. washeluting with 9:1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-338a8479968e49a5ae2c6a22218ce001
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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