Acetic Acid → 4-[3-(Cyclopropylmethyl-amino)-pyrazol-1-yl]-benzonitrile

HRID 1191095노트

반응식

HRID 1191095 반응식
[NH2:1][C:2]1[CH:6]=[CH:5][N:4]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[N:3]=1.C(O)(=O)C.[CH:19]1([CH:22]=O)[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH:19]1([CH2:22][NH:1][C:2]2[CH:6]=[CH:5][N:4]([C:7]3[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=3)[N:3]=2)[CH2:21][CH2:20]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 123114CyclopropanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 42656760685094-19-3

생성물 1

HCID 598289114-[3-(Cyclopropylmethyl-amino)-pyrazol-1-yl]-benzonitrile수율 54%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

Dissolve 4-(3-amino-pyrazol-1-yl)-benzonitrile (200 mg) in 1,2-dichloroethane (12 mL). Add acetic acid (0.36 mL) and cyclopropanecarboxaldehyde (0.08 mL, 1.06 mmol) and stir the mixture at room temperature under a nitrogen atmosphere for 40 min. Add sodium triacetoxyborohydride (674 mg, 3.18 mmol) and stir for 3 h at room temperature. Quench the reaction with water. Extract the mixture three timed with EtOAc. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to obtain the desired intermediate (136 mg, 54%) that was used without further purification.

후처리

  1. customQuench
  2. customthe reaction with water
  3. extractionExtract the mixture three
  4. dry with materialDry the combined organic extracts over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

출처 및 근거

ORD 기록
ord-b29284e0efd447da9e161b530ed43750
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680091B2

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