Methanesulfonamide → HCID 47269479, compound

HRID 2242196Notes

Reaction equation

HRID 2242196 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7](O)=[O:8])[CH:5]=1.[CH3:14][S:15]([NH2:18])(=[O:17])=[O:16].Cl.CN(C)CCCN=C=NCC>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([NH:18][S:15]([CH3:14])(=[O:17])=[O:16])=[O:8])[CH:5]=1

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 47269479HCID 47269479, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of isophthalic acid monomethyl ester (500.0 mg, 2.8 mmol), methanesulfonamide (340 mg, 3.6 mmol) and DMAP (440 mg, 3.6 mmol) in anhydrous dichloromethane (30 mL) was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (690 mg, 3.6 mmol). The mixture was allowed to stir for 12 hours at room temperature and then concentrated under reduced pressure. The residue was chromatographed on a Biotage 40M eluting with 2% methanol/98% dichloromethane to provide the titled compound. MS (EST) m/e 259 (M+H)+, 257 (M−H)−; 1H NMR (300 MHz, CD3OD) δ ppm 3.36 (s, 3 H) 3.95 (s, 3 H) 7.64 (t, J=7.80 Hz, 1 H) 8.13 (dd, J=7.80, 1.36 Hz, 1 H) 8.25 (m, 1 H) 8.55 (m, 1 H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was chromatographed on a Biotage 40M
  3. washeluting with 2% methanol/98% dichloromethane

Sources & evidence

ORD record
ord-afa1952d0b1a4d46918c10f56fd19df5
Source dataset
uspto-grants-2010_03
Patent number
US07671076B2

Reaction notes

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