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

HRID 2400564노트

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HRID 2400564 반응식
[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

참가 물질

7

반응물 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 27470481-(4-Methylbenzyl)-5-methyl-1H-pyrazole-3-carboxylic acid2회

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e0ec9b153a0c424ab0660989703d2969
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08796253B2

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