Dimethylformamide → 4-{[6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carbonyl]-amino}-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester

HRID 467650ノート

反応式

HRID 467650 の反応式
C[CH2:2][N:3]=[C:4]=[N:5]CCCN(C)C.[CH:12]1[CH:13]=[CH:14][C:15]2[N:20](O)N=N[C:16]=2[CH:17]=1.[CH3:22][O:23][C:24]([C:26]1[C:30]([NH2:31])=[CH:29][N:28]([CH3:32])[N:27]=1)=[O:25].C([N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])C.CN([CH:43]=[O:44])C>>[CH3:22][O:23][C:24]([C:26]1[C:30]([NH:31][C:43]([C:39]2[C:38]([NH:35][C:36]3[CH:37]=[N:5][CH:4]=[N:3][CH:2]=3)=[CH:17][CH:16]=[C:15]([CH:14]3[CH2:13][CH2:12]3)[N:20]=2)=[O:44])=[CH:29][N:28]([CH3:32])[N:27]=1)=[O:25]

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7017722methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate

生成物 1

HCID 700992004-{[6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carbonyl]-amino}-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester収率 69%

実験手順

To a stirred solution of A-2 (600 mg, 2.34 mmol) in DMF (10 ml) was added EDCI (672 mg, 3.51 mmol) and HOBt (538 mg, 3.51 mmol) at 25° C. Stirring was continued for 10 min. 4-Amino-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester (362 mg, 2.35 mmol) and triethylamine (0.8 ml, 5.35 mmol) were subsequently added to the above solution. The reaction mixture was stirred at 25° C. overnight, then quenched with water (8 ml), and extracted with CH2Cl2. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and evaporated. The crude product thus obtained was purified by column chromatography over silica gel (2% MeOH/CH2Cl2) to provide the title compound (642 mg, 69%) as yellow sticky solid.

後処理

  1. stirringThe reaction mixture was stirred at 25° C. overnight
  2. customquenched with water (8 ml)
  3. extractionextracted with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product thus obtained
  9. customwas purified by column chromatography over silica gel (2% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-b78b5a48fed941d9a5eb2eba81dbeeb9
出典データセット
uspto-grants-2014_01
特許番号
US08623866B2

反応ノート

読み込み中…