2-Methylbenzenesulfonamide → HCID 18444621, compound

HRID 490416

Reaction equation

HRID 490416 reaction equation
[F:1][CH:2]([F:28])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]([CH2:18][C:19]3[CH:20]=[C:21]([C:25]([OH:27])=O)[O:22][C:23]=3[CH3:24])[CH3:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[CH3:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[S:36]([NH2:39])(=[O:38])=[O:37].Cl.CN(C)CCCN=C=NCC>CN(C1C=CN=CC=1)C.ClCCl.C(#N)C>[F:28][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]([CH2:18][C:19]3[CH:20]=[C:21]([C:25]([NH:39][S:36]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[CH3:29])(=[O:37])=[O:38])=[O:27])[O:22][C:23]=3[CH3:24])[CH3:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 69242-MethylbenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184445654-([(4'-Difluoromethoxy-biphenyl-4-yl)-methyl-amino]-methyl)-5-methyl-furan-2-carboxylic acid

Product 1

HCID 18444621HCID 18444621, compoundYield 9.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 4-{[(4′-difluoromethoxy-biphenyl-4-yl)-methyl-amino]-methyl}-5-methyl-furan-2-carboxylic acid (176) (21 mg, 0.054 mmoles), 2-methyl-benzenesulphonamide (19 mg, 0.108 mmoles) and 4-(N,N-dimethylamino)-pyridine (1 mg) in a mixture of dichloromethane (8 ml) and acetonitrile (2 ml) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (11.4 mg, 0.060 mmoles). The mixture was stirred at room temperature for 18 hours under an argon atmosphere. The reaction mixture was concentrated in vacuo and the residue was purified by HPLC to afford compound 177 (2.9 mg) as a solid. LC/MS System D; Rt=11.21 mins, m/z (ES+)=541 (M+H for C28H26F2N2O5S).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-c34f0852176a4984b1f9d759be30080c
Source dataset
uspto-grants-2009_05
Patent number
US07528157B2

Linked notes

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