Ethyl Acetate → 4-(Aminosulfonyl)-N-{(cis)-2-[({[(3-chlorophenyl)sulfonyl]amino)acetyl)amino]cyclohexyl}benzamide

HRID 1825032

反応式

HRID 1825032 の反応式
Br.[NH2:2][CH2:3][C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[NH:13][C:14](=[O:25])[C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1)=[O:5].[Cl:26][C:27]1[CH:28]=[C:29]([S:33](Cl)(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1.CCOC(C)=O>CN(C=O)C>[NH2:24][S:21]([C:18]1[CH:17]=[CH:16][C:15]([C:14]([NH:13][C@@H:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C@@H:7]2[NH:6][C:4](=[O:5])[CH2:3][NH:2][S:33]([C:29]2[CH:30]=[CH:31][CH:32]=[C:27]([Cl:26])[CH:28]=2)(=[O:35])=[O:34])=[O:25])=[CH:20][CH:19]=1)(=[O:23])=[O:22]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 179093-Chlorobenzenesulphonyl chlorideHCID 68830145N-(cis)-{2-[(aminoacetyl)amino]cyclohexyl}-4-(aminosulfonyl)benzamide hydrogen bromide

生成物 1

HCID 688280684-(Aminosulfonyl)-N-{(cis)-2-[({[(3-chlorophenyl)sulfonyl]amino)acetyl)amino]cyclohexyl}benzamide収率 29.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N-(cis)-{2-[(aminoacetyl)amino]cyclohexyl}-4-(aminosulfonyl)benzamide hydrogen bromide, (61b), (70 mg) was dissolved in DMF (2.5 mL) prior to the addition of 3-chlorobenzenesulfonyl chloride (51 mg). After stirring overnight, EtOAc was added and the solution was washed with 1N HCl. The EtOAc was dried, filtered, and concentrated. Reverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue provided the title benzamide (25 mg). MS found: (M+H)+=530.1.

後処理

  1. washthe solution was washed with 1N HCl
  2. dry with materialThe EtOAc was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customReverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue

出典と根拠

ORDレコード
ord-4a114e50f4384496b75c056b290fb627
出典データセット
uspto-grants-2006_05
特許番号
US07045521B2

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