Sodium Iodide → Brexpiprazole

HRID 1364263노트

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HRID 1364263 반응식
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13](=[O:17])[NH:14]2)=[CH:9][CH:8]=1.Cl.[S:19]1[CH:23]=[CH:22][C:21]2[C:24]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[CH:25][CH:26]=[CH:27][C:20]1=2.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.CN(C)C=O>[S:19]1[CH:23]=[CH:22][C:21]2[C:24]([N:28]3[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]4[CH:16]=[C:15]5[C:10]([CH:11]=[CH:12][C:13](=[O:17])[NH:14]5)=[CH:9][CH:8]=4)[CH2:30][CH2:29]3)=[CH:25][CH:26]=[CH:27][C:20]1=2

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 566050407-(4-Chlorobutoxy)-1H-quinolin-2-oneHCID 574825411-(1-Benzothiophen-4-yl)piperazine hydrochloride

생성물 1

HCID 11978813Brexpiprazole

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

A mixture of 9.0 g of 7-(4-chlorobutoxy)-1H-quinolin-2-one, 10 g of 1-benzo[b]thiophene-4-yl-piperazine hydrochloride, 14 g of potassium carbonate, 6 g of sodium iodide and 90 ml of dimethylformamide was stirred for 2 hours at 80° C. Water was added to the reaction solution and precipitated crystals were separated by filtration. The crystals were dissolved in a mixed solvent of dichloromethane and methanol, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=100:3). Recrystallized from ethanol, 13.6 g of 7-[4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butoxy-]-1H-quinolin-2-one in the form of a white powder was obtained.

후처리

  1. customprecipitated crystals
  2. customwere separated by filtration
  3. dissolutionThe crystals were dissolved in a mixed solvent of dichloromethane and methanol
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=100:3)
  7. customRecrystallized from ethanol, 13.6 g of 7-[4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butoxy-]-1H-quinolin-2-one in the form of a white powder
  8. customwas obtained

출처 및 근거

ORD 기록
ord-14688980d6e949338dcfa049d55e4695
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888362B2

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