1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 3-{1-(1,3-Benzodioxol-5-yl)-2-[(2-methoxy-4-methylphenyl)sulfonamido]-2-oxoethyl}-5-bromo-1-methyl-1H-indole

HRID 381328ノート

反応式

HRID 381328 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([Br:23])[CH:21]=4)[N:16]([CH3:24])[CH:15]=3)[C:11]([O-])=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:25][O:26][C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][C:28]=1[S:34]([NH2:37])(=[O:36])=[O:35].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([Br:23])[CH:21]=4)[N:16]([CH3:24])[CH:15]=3)[C:11]([NH:37][S:34]([C:28]3[CH:29]=[CH:30][C:31]([CH3:33])=[CH:32][C:27]=3[O:26][CH3:25])(=[O:35])=[O:36])=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1

参加物

6

反応物 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 50933692-Methoxy-4-methylbenzenesulfonamideHCID 867575132-(1,3-benzodioxol-5-yl)-2-(5-bromo-1-methyl-1H-3-indolyl)acetate

生成物 1

HCID 224672163-{1-(1,3-Benzodioxol-5-yl)-2-[(2-methoxy-4-methylphenyl)sulfonamido]-2-oxoethyl}-5-bromo-1-methyl-1H-indole

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

4 -Dimethylaminopyridine (151 mg) was added to a solution of 2-(1,3-benzodioxol-5-yl)-2-(5-bromo-1-methyl-1H-3-indolyl)acetate acid (the product of Example 68, 480 mg. 1.24 mmol) in anhydrous dichloromethane (10 ml) at ambient temperature. 2-Methoxy-4-methyl-1-benzenesulfonamide (from Preparation 11, 300 mg, 1.48 mmol) was added to the solution, followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (355 mg. 1.85 mmol), and stirring was continued for 20 hours. The solution was washed twice with 2N hydrochloric acid, and dried (magnesium sulphate) and the solvents removed in vacuo. The residue was flash chromatographed using 1% methanol in dichloromethane as eluant, and crystallised from dichloromethane and diethyl ether mixture to give the subtitle compound (535 mg).

後処理

  1. customat ambient temperature
  2. washThe solution was washed twice with 2N hydrochloric acid
  3. dry with materialdried (magnesium sulphate)
  4. customthe solvents removed in vacuo
  5. customchromatographed
  6. customcrystallised from dichloromethane and diethyl ether mixture

出典と根拠

ORDレコード
ord-c9bc1abbdd7a4e409f1a59d34823ad20
出典データセット
uspto-grants-2001_10
特許番号
US06306852B1

反応ノート

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