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Diisopropylethylamine → 5-amino-1-[5-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-2-methyl-phenyl]-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 1723953
ノート
印刷プレビュー

反応式

HRID 1723953 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([NH2:11])[N:8]([C:12]2[CH:17]=[C:16]([C:18]([OH:20])=O)[CH:15]=[CH:14][C:13]=2[CH3:21])[N:7]=1)=[O:5])[CH3:2].[NH2:22][C:23]1[C:24]([O:38][CH3:39])=[C:25]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:26]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:28]=1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([NH2:11])[N:8]([C:12]2[CH:17]=[C:16]([C:18](=[O:20])[NH:22][C:23]3[CH:28]=[C:27]([C:29]([CH3:31])([CH3:32])[CH3:30])[CH:26]=[C:25]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:24]=3[O:38][CH3:39])[CH:15]=[CH:14][C:13]=2[CH3:21])[N:7]=1)=[O:5])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamideHCID 57559704HCID 57559704、化合物

生成物 1

HCID 116995445-amino-1-[5-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-2-methyl-phenyl]-1H-pyrazole-3-carboxylic acid ethyl ester収率 48%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

5-Amino-1-(5-carboxy-2-methyl-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (46 mg, 0.159 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate (HATU) (67 mg, 0.175 mmol) were combined in DMF (500 μL) and stirred for 5 min at room temperature N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide (48 mg, 0.175 mmol) was added to the reaction mixture followed by i-Pr2NEt (83 μL, 0.477 mmol). The solution was stirred at room temperature for 48 h then poured onto saturated NaHCO3. The aqueous layer was extracted with CH2Cl2 and the combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by semi-prep HPLC provided the title compound (41 mg, 48%) as a yellow solid (TFA salt): mp 104-111° C. (dec.); ESI MS m/z 544 [C26H33N5O6S+H]+; HPLC>98%, tR=20.79 min.

後処理

  1. additionwas added to the reaction mixture
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. dry with materialthe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by semi-prep HPLC

出典と根拠

ORDレコード
ord-a3d5b5a791224f7b93395262553693ad
出典データセット
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07485657B2

反応ノート

読み込み中…

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