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

HRID 1191095ノート

反応式

HRID 1191095 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b29284e0efd447da9e161b530ed43750
出典データセット
uspto-grants-2014_03
特許番号
US08680091B2

反応ノート

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