Triethylamine → N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide

HRID 38230

반응식

HRID 38230 반응식
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]([OH:15])=O)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.Cl.[CH3:25][NH:26][O:27][CH3:28].CCN(CC)CC>C(Cl)Cl.CN(C=O)C>[CH3:28][O:27][N:26]([CH3:25])[C:13]([C:11]1[CH:10]=[N:9][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:17][CH:16]=2)[CH:12]=1)=[O:15]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 435653621-[(4-methoxyphenyl)methyl]-1H-pyrazole-4-carboxylic acid

생성물 1

HCID 86642328N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide수율 98.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

According to Scheme 3 Step 1: A solution of 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylic acid (34.4 mmol, 8.00 g), oxalyl chloride (68.9 mmol, 5.92 mL) and a drop of DMF in DCM (80 mL) was stirred for 1 hour at room temperature. After evaporation, the crude product was dissolved in DCM (30 mL) and was added at 0° C. to a solution of N,O-dimethylhydroxylamine hydrochloride (103 mmol, 6.31 g) in DCM (100 mL) followed by Et3N (138 mmol, 19.2 mL). The reaction mixture was stirred for 1 hour at room temperature. The reaction was quenched with a saturated solution of Na2CO3 (300 mL) and the aqueous phase was extracted with DCM. The organic phase was dried over MgSO4, was filtered and was concentrated to yield N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide (33.8 mmol, 9.30 g, 98%) as a beige solid.

후처리

  1. customAfter evaporation
  2. dissolutionthe crude product was dissolved in DCM (30 mL)
  3. customThe reaction was quenched with a saturated solution of Na2CO3 (300 mL)
  4. extractionthe aqueous phase was extracted with DCM
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationwas filtered
  7. concentrationwas concentrated

출처 및 근거

ORD 기록
ord-1a49b91c957744b1b47ec64285602453
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524718B2

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