Oxalyl chloride → N-(4-benzoylpyrrolidino)-1-(4-methoxyphenyl)-3-(methylthio)-1H-pyrazole-5-carboxamide

HRID 394789

反応式

HRID 394789 の反応式
[C:1](Cl)(=O)[C:2](Cl)=O.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]([C:20]([OH:22])=O)=[CH:18][C:17]([S:23][CH3:24])=[N:16]2)=[CH:11][CH:10]=1.N[C:26]1[CH:38]=[CH:37][C:29]([C:30](N2CCCC2)=[O:31])=[CH:28][CH:27]=1>CN(C=O)C.C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:30]([CH:2]1[CH2:1][N:15]([NH:16][C:20]([C:19]2[N:15]([C:12]3[CH:11]=[CH:10][C:9]([O:8][CH3:7])=[CH:14][CH:13]=3)[N:16]=[C:17]([S:23][CH3:24])[CH:18]=2)=[O:22])[CH2:12][CH2:11]1)(=[O:31])[C:29]1[CH:28]=[CH:27][CH:26]=[CH:38][CH:37]=1

参加物

7

反応物 3

HCID 65578Oxalyl chlorideHCID 5778004-(Pyrrolidin-1-ylcarbonyl)anilineHCID 181773011-(4-Methoxyphenyl)-3-methylthio-1H-pyrazole-5-carboxylic acid

生成物 1

HCID 10238249N-(4-benzoylpyrrolidino)-1-(4-methoxyphenyl)-3-(methylthio)-1H-pyrazole-5-carboxamide収率 212.6%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Oxalyl chloride (140 μl, 1.6 mmol) and dry DMF (2 drops) were added at room temperature to 1-(4-methoxyphenyl)-3-methylthio-1H-pyrazole-5-carboxylic acid (275 mg, 1.0 mmol) in dry CH2Cl2 (8 mL) and stirred for 100 minutes under N2. The resulting solution was evaporated and placed briefly under high vacuum before redissolving in CH2Cl2 (8 mL). (4-aminobenzoyl)pyrrolidine (198 mg, 1.0 mmol) was added, followed by 4-dimethylaminopyridine (190 mg, 1.6 mmol). The resulting mixture was stirred at room temperature for 17 hours, diluted with CH2Cl2, and extracted with H2O. The aqueous extract was extracted with CH2Cl2, the combined organic extracts were extracted with brine. The organic layer was dried over Na2SO4, filtered, and evaporated. The crude product was chromatographed on silica gel (75-100% EtOAc/hexanes) to yield the desired product (464 mg, 100%). 1H NMR (CDCl3): δ 7.91 (bs, 1H), 7.44 (s, 4H), 7.39 (d, 2H, J=8.8), 6.97 (d, 2H, J=8.8), 6.83 (s, 1H), 3.84 (s, 3H), 3.62 (t, 2H, J=6.6), 3.42 (t, 2H, J=6.6), 2.57 (s, 3H), 1.91 (m, 4H).

後処理

  1. customThe resulting solution was evaporated
  2. dissolutionbefore redissolving in CH2Cl2 (8 mL)
  3. stirringThe resulting mixture was stirred at room temperature for 17 hours
  4. extractionextracted with H2O
  5. extractionThe aqueous extract
  6. extractionwas extracted with CH2Cl2
  7. extractionthe combined organic extracts were extracted with brine
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude product was chromatographed on silica gel (75-100% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-57715c0821564bb1a4642acef7f73b57
出典データセット
uspto-grants-2003_08
特許番号
US06602895B2

関連ノート

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