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

HRID 1619277ノート

反応式

HRID 1619277 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-72e341f6e5734187a26d1bd0b3729755
出典データセット
uspto-grants-2014_07
特許番号
US08772285B2

反応ノート

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