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

HRID 38230

反応式

HRID 38230 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1a49b91c957744b1b47ec64285602453
出典データセット
uspto-grants-2013_09
特許番号
US08524718B2

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