2-Methylbenzenesulfonamide → HCID 18444615, compound

HRID 2266858Notes

Reaction equation

HRID 2266858 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][CH2:17][C:18]3[CH:19]=[C:20]([C:24](O)=[O:25])[O:21][C:22]=3[CH3:23])=[CH:12][CH:11]=2)=[N:8][CH:9]=1.[C:27]1([CH3:37])[C:28]([S:33]([NH2:36])(=[O:35])=[O:34])=[CH:29][CH:30]=[CH:31][CH:32]=1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>O1CCCC1.CN(C1C=CN=CC=1)C>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][CH2:17][C:18]3[CH:19]=[C:20]([C:24]([NH:36][S:33]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[CH3:37])(=[O:34])=[O:35])=[O:25])[O:21][C:22]=3[CH3:23])=[CH:12][CH:11]=2)=[N:8][CH:9]=1

Participants

7

Reactant 4

HCID 69242-MethylbenzenesulfonamideHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68680725HCID 68680725, compound

Product 1

HCID 18444615HCID 18444615, compoundYield 2.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4-{[4-(5-methoxy-pyridin-2-yl)-phenylamino]-methyl}-5-methyl-furan-2-carboxylic acid hydrochloride salt (166) (30 mg, 0.08 mmoles) in tetrahydrofuran (5 ml) was treated with toluene-2-sulphonamide (41 mg, 0.24 mmoles), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (34 mg, 0.176 mmoles) and 4-(N,N-dimethylamino)-pyridine (10 mg, 0.08 mmoles) and the mixture stirred at room temperature for 16 hours. Triethylamine (24.3 mg, 0.24 mmoles) was added and the mixture was stirred for a further 18 hours. The reaction mixture was concentrated and the residue was purified by HPLC to afford compound 167 as a yellow glass (1.1 mg)). LC/MS System A; Rt=2.72 mins, m/z (ES+)=492 (M+H for C26H25N3O5S) and m/z (ES−)=490 (M−H for C26H25N3O5S).

Workup

  1. stirringthe mixture was stirred for a further 18 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-a118f17b31a745f78bc72adf89c3642c
Source dataset
uspto-grants-2010_12
Patent number
US07858644B2

Reaction notes

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