2-Methyltetrahydrofuran → HCID 57501579, 화합물

HRID 1518657노트

반응식

HRID 1518657 반응식
[CH2:1]1[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]3[CH:18]=[CH:19][C:20]([NH:22][C:14]=3[CH:13]=2)=[O:21])[CH2:5][CH2:4][N:3]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=2[Cl:30])[CH2:2]1.CC(C)([O-])C.[K+].CC1CCCO1.Cl[C:44]([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])=[O:45]>O>[C:44](=[O:45])([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[O:21][C:20]1[CH:19]=[CH:18][C:15]2[C:14](=[CH:13][C:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][N:6]3[CH2:5][CH2:4][N:3]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=4[Cl:30])[CH2:2][CH2:1]3)=[CH:17][CH:16]=2)[N:22]=1

참가 물질

6

반응물 4

HCID 73012-MethyltetrahydrofuranHCID 22466Hexyl chloroformateHCID 10114519DehydroaripiprazoleHCID 23665647Potassium tert-butoxide

생성물 1

HCID 57501579HCID 57501579, 화합물

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a mixture of dehydro-aripiprazole (1.5 g, 3.4 mmol), potassium tert-butoxide (0.75 g, 6.7 mmol) and 2-methyltetrahydrofuran (30 mL) at 0° C. was added hexyl chloroformate (1.32 mL, 8.1 mmol). The reaction mixture was stirred for 2 h, allowed to self warm to room temperature and stirred for a further 4 h. The reaction mixture was then diluted with water and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and evaporated. The residue was further purified on silica eluting with ethyl acetate/tetrahydrofuran and the major product containing fractions evaporated to give a yellow solid. This was triturated in heptane (30 mL) for 2.5 h, filtered and dried to give Compound-328 (1.55 g) as a white solid.

후처리

  1. stirringstirred for a further 4 h
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was further purified on silica eluting with ethyl acetate/tetrahydrofuran
  7. additionthe major product containing fractions
  8. customevaporated
  9. customto give a yellow solid
  10. customThis was triturated in heptane (30 mL) for 2.5 h
  11. filtrationfiltered
  12. customdried
  13. customto give Compound-328 (1.55 g) as a white solid

출처 및 근거

ORD 기록
ord-bafcc91a7f6247bab3c5d25768dae20f
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09072788B2

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