Acetic Acid → 2-(4-Cyclopropylpiperazin-1-yl)-5-pyrrolidin-1-ylmethylbenzooxazole

HRID 1619277노트

반응식

HRID 1619277 반응식
[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[O:11][C:12]4[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO.C1COCC1>[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[O:11][C:12]4[CH:18]=[CH:17][C:16]([CH2:19][N:21]5[CH2:25][CH2:24][CH2:23][CH2:22]5)=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5003444Sodium cyanoborohydrideHCID 595887962-(4-Cyclopropylpiperazin-1-yl)benzooxazole-5-carboxaldehyde

생성물 1

HCID 237289312-(4-Cyclopropylpiperazin-1-yl)-5-pyrrolidin-1-ylmethylbenzooxazole수율 40%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

To a solution of 2-(4-cyclopropylpiperazin-1-yl)benzooxazole-5-carboxaldehyde (400 mg, 1.48 mmol) and pyrrolidine (210 mg, 2.96 mmol) in CH3OH/THF (36 mL, 1:3) was added acetic acid (142 mg, 2.37 mmol), followed by NaCNBH3 (137 mg, 2.37 mmol). The mixture was heated at reflux for 12 h. The volatiles were removed and the residue was diluted with water (5 mL). The resulting mixture was extracted with CH2Cl2 (3×10 mL) and the combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by column chromatography on silica gel (elute: 2% dichloromethane in methanol) to give 193 mg (40%) of 2-(4-cyclopropylpiperazin-1-yl)-5-pyrrolidin-1-ylmethylbenzooxazole.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 h
  3. customThe volatiles were removed
  4. additionthe residue was diluted with water (5 mL)
  5. extractionThe resulting mixture was extracted with CH2Cl2 (3×10 mL)
  6. dry with materialthe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (elute: 2% dichloromethane in methanol)

출처 및 근거

ORD 기록
ord-72e341f6e5734187a26d1bd0b3729755
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772285B2

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