Triethylamine → HCID 60208914, compound

HRID 548058Notes

Reaction equation

HRID 548058 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][NH:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:2]1.Cl[S:18]([C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1)(=[O:20])=[O:19].C(N(CC)CC)C>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][N:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[S:18]([C:21]2[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=2)(=[O:20])=[O:19])=[CH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4738388Methyl 4-(Chlorosulfonyl)benzoateHCID 60208913HCID 60208913, compound

Product 1

HCID 60208914HCID 60208914, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

110 mg of 1-(furan-3-yl)-N-(4-methoxybenzyl)methanamine (example 5-27a) was mixed with methyl 4-(chlorosulfonyl)benzoate (example 5-10c) (117 mg, 0.5 mmol) and triethyl amine (100 uL) in DCM (5 mL). The mixture was stirred overnight at ambient temperature and concentrated. The residue was re-dissolved in ethyl acetate (20 mL), washed with 1N HCl (aq., 2 mL), followed by water (5 mL) and brine (5 mL) then dried over magnesium sulfate. The crude product was purified by preparative TLC (40% Ethyl Acetate/hexanes) to give methyl 4-(N-(furan-3-ylmethyl)-N-(4-methoxybenzyl)sulfamoyl)benzoate as a white solid. Saponification as in example 5-10 gave 4-(N-(furan-3-ylmethyl)-N-(4-methoxybenzyl)sulfamoyl)benzoic acid as a white crystalline solid (68 mg, 64% yield). MS (M−H, 400.1); 1H NMR (400 MHz, DMSO-d6): δ, ppm: 3.72 (s, 3H), 4.13 (s, 2H), 4.26 (s, 2H), 5.99 (s, 1H), 6.87 (m, 4H), 6.87 (d, 2H, J=8.8 Hz), 7.13 (d, 2H, J=8.8 Hz), 7.39 (s, 1H), 7.49 (s, 1H), 7.95 (d, 2H, J=8.4 Hz), 8.09 (d, 2H, J=8.8 Hz).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was re-dissolved in ethyl acetate (20 mL)
  3. washwashed with 1N HCl (aq., 2 mL)
  4. dry with materialthen dried over magnesium sulfate
  5. customThe crude product was purified by preparative TLC (40% Ethyl Acetate/hexanes)

Sources & evidence

ORD record
ord-3f0df5496966444aa11c08814c75be86
Source dataset
uspto-grants-2011_05
Patent number
US07939671B2

Reaction notes

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