Bumetanide → N,N-diethylaminocarbonylmethyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate

HRID 1676909

反応式

HRID 1676909 の反応式
[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[C:8]([C:23]([OH:25])=[O:24])[CH:9]=[C:10]([S:19]([NH2:22])(=[O:21])=[O:20])[C:11]=1[O:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1.Cl[CH2:27][C:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[O:29].C(N(CC)CC)C.[I-].[Na+]>CN(C)C=O.ClCCl>[NH2:22][S:19]([C:10]1[CH:9]=[C:8]([CH:7]=[C:6]([NH:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:11]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:23]([O:25][CH2:27][C:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[O:29])=[O:24])(=[O:21])=[O:20]

参加物

7

反応物 4

HCID 2471BumetanideHCID 5238Sodium IodideHCID 8471TriethylamineHCID 16844Chloro-N,N-diethylacetamide

生成物 1

HCID 16657241N,N-diethylaminocarbonylmethyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate収率 63.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
95 °C

実験手順

Bumetanide (1.2 g, 3.29 mmol) was dissolved in dimethylformamide (12 mL) and 2-chloro-N,N-diethylacetamide (500 mg, 3.35 mmol) was added followed by triethylamine (0.68 mL) and sodium iodide (500 mg 3.33 mmol). The reaction was heated to 95° C. for 8 hours, at which time TLC and LC/MS indicated the reaction was complete. The reaction was cooled to room temperature brought up in dichloromethane and washed with water, saturated ammonium chloride and reduced to a thick slurry. To the slurry was added water (25 mL), and the resultant solids precipitated from the solution. The product was filtered and dried in a vacuum oven at 50° C. for 12 hours to yield 1.0 g of N,N-diethylaminocarbonylmethyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate.

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with water, saturated ammonium chloride
  3. additionTo the slurry was added water (25 mL)
  4. customthe resultant solids precipitated from the solution
  5. filtrationThe product was filtered
  6. customdried in a vacuum oven at 50° C. for 12 hours

出典と根拠

ORDレコード
ord-57c9f7a2ffad4d7c8419fcd840a53bf9
出典データセット
uspto-grants-2011_08
特許番号
US08008283B2

関連ノート

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