N,N-Dimethylsulfamide → N-[4-(4'-Methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carbonyl]-dimethylamino-sulphonamide

HRID 460084ノート

反応式

HRID 460084 の反応式
[CH3:1][N:2]([CH3:7])[S:3]([NH2:6])(=[O:5])=[O:4].Cl.CN(C)CCCN=C=NCC.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]3[CH:37]=[C:38]([C:42](O)=[O:43])[O:39][C:40]=3[CH3:41])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:29]=[CH:30][C:31]([O:34][CH2:35][C:36]3[CH:37]=[C:38]([C:42]([NH:6][S:3]([N:2]([CH3:7])[CH3:1])(=[O:5])=[O:4])=[O:43])[O:39][C:40]=3[CH3:41])=[CH:32][CH:33]=2)=[CH:26][CH:27]=1

参加物

6

反応物 3

HCID 134472N,N-DimethylsulfamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 104272364-(4'-Methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid

生成物 1

HCID 18444679N-[4-(4'-Methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carbonyl]-dimethylamino-sulphonamide収率 35.7%

試薬・触媒・溶媒 2

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

実験手順

N,N-Dimethylsulphamide (73 mg, 0.59 mmoles), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (31 mg, 0.162 mmoles) and dimethyl-pyridin-4-yl-amine (1 mg) were added to a stirred solution of 4-(4′-methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid (4)(50 mg, 0.148 mmoles) in dichloromethane (20 ml). The mixture was stirred under an argon atmosphere for 18 hours. After evaporation of the solvent, the residue was partitioned between dichloromethane and water. The aqueous phase was separated and extracted with dichloromethane. The combined extracts were washed with 1M aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, brine and dried (MgSO4). Evaporation of the solvent afforded the crude product, which was purified by HPLC (gradient: 30% acetonitrile/70% water containing 0.1% trifluoroacetic acid to 98% acetonitrile/2% water at a rate of 1%/min) to afford compound 122(23.5 mg) as a white solid. LC/MS System C: Rt=3.67 mins, m/z (ES−)=443 ((M−H) for C22H24N2O6S).

後処理

  1. customAfter evaporation of the solvent
  2. customthe residue was partitioned between dichloromethane and water
  3. customThe aqueous phase was separated
  4. extractionextracted with dichloromethane
  5. washThe combined extracts were washed with 1M aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, brine
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the solvent
  8. customafforded the crude product, which
  9. customwas purified by HPLC (gradient

出典と根拠

ORDレコード
ord-38a534a2c488487e942b7f37aed9a434
出典データセット
uspto-grants-2007_03
特許番号
US07196089B2

反応ノート

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