Acetic Acid → 1-(2-Fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboximidamide

HRID 570519ノート

反応式

HRID 570519 の反応式
[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][N:5]1[C:9]2[CH2:10][CH2:11][CH2:12][C:8]=2[C:7]([C:13]#[N:14])=[N:6]1.C[O-].[Na+].C(O)(=O)C.[Cl-].[NH4+:27]>CO>[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][N:5]1[C:9]2[CH2:10][CH2:11][CH2:12][C:8]=2[C:7]([C:13](=[NH:27])[NH2:14])=[N:6]1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 712853771-(2-Fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carbonitrile

生成物 1

HCID 866920921-(2-Fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboximidamide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Under a nitrogen atmosphere, 3.600 g (14.92 mmol) of 1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carbonitrile were dissolved in 37 ml of absolute methanol. 1.306 (24.17 mmol) of sodium methoxide were added and the mixture was stirred at RT for 4 h. 1.452 g (24.17 mmol) of acetic acid and 1.197 g (22.38 mmol) of ammonium chloride were added and the suspension was stirred at 50° C. overnight. The reaction mixture was concentrated and the residue was suspended in 100 ml of water and 25 ml of 1N hydrochloric acid. The mixture was extracted with dichloromethane. The aqueous phase was basified (pH=12) with 2N sodium hydroxide solution and extracted three times with a mixture of dichloromethane/methanol (v/v=8:2). The combined organic phases were dried with sodium sulphate and concentrated, toluene was added and the mixture was again concentrated to dryness. 1.94 g (50% of theory) of the target compound were obtained.

後処理

  1. stirringthe suspension was stirred at 50° C. overnight
  2. concentrationThe reaction mixture was concentrated
  3. extractionThe mixture was extracted with dichloromethane
  4. extractionextracted three times
  5. additionwith a mixture of dichloromethane/methanol (v/v=8:2)
  6. dry with materialThe combined organic phases were dried with sodium sulphate
  7. concentrationconcentrated
  8. additiontoluene was added
  9. concentrationthe mixture was again concentrated to dryness
  10. custom1.94 g (50% of theory) of the target compound were obtained

出典と根拠

ORDレコード
ord-47d895f860c447419f516569f22a27ee
出典データセット
uspto-grants-2015_05
特許番号
US09023849B2

反応ノート

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