Ammonia → 5-Methyl-1-(4-methylbenzyl)-1H-pyrazole-3-carboxamide

HRID 2400564ノート

反応式

HRID 2400564 の反応式
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]([OH:17])=O)[CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH3:24]>ClCCl.CN(C=O)C.O1CCOCC1>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]([NH2:24])=[O:17])[CH:3]=1

参加物

7

反応物 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 27470481-(4-Methylbenzyl)-5-methyl-1H-pyrazole-3-carboxylic acid2 回

生成物 1

HCID 595047015-Methyl-1-(4-methylbenzyl)-1H-pyrazole-3-carboxamide

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a mechanically stirred solution of 5-methyl-1-(4-methylbenzyl)-1H-pyrazole-3-carboxylic acid (Intermediate B, 500 mg, 2.17 mmol) in dichloromethane (15 mL) was added dropwise oxalylchloride (950 μL, 10.9 mmol) and one drop DMF. After stirring at rt for 1 h, all volatiles were removed in vacuo. The crude acid chloride thus obtained was re-dissolved in dioxane (10 mL) and added dropwise to aqueous ammonia (33%, 6.4 mL) at 0° C. After the addition was complete, the reaction mixture was stirred at rt for 30 minutes. A white precipitate formed which was collected by filtration and washed with water. The title compound was obtained after drying in vacuo (436 mg, 89%): 1H NMR (400 MHz, DMSO-d6) δ 7.37 (broad s, 1H), 7.14 (d, 2H, and broad s, 1H), 7.02 (d, 2H), 6.43 (s, 1H), 5.28 (s, 2H), 2.27 (s, 3H), 2.19 (s, 3H); ES-MS m/z 230 (MH)+; HPLC RT (Method E) 1.39 min.

後処理

  1. customall volatiles were removed in vacuo
  2. customThe crude acid chloride thus obtained
  3. additionAfter the addition
  4. stirringthe reaction mixture was stirred at rt for 30 minutes
  5. customA white precipitate formed which
  6. filtrationwas collected by filtration
  7. washwashed with water

出典と根拠

ORDレコード
ord-e0ec9b153a0c424ab0660989703d2969
出典データセット
uspto-grants-2014_08
特許番号
US08796253B2

反応ノート

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