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

HRID 490383
Notes
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Reaction equation

HRID 490383 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c092f164984e44a99bd721fbabd3e1d8
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07528157B2

Reaction notes

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