3-Aminobenzenesulfonic acid → HCID 18405376, compound

HRID 1018368Notes

Reaction equation

HRID 1018368 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]12([CH2:17][CH2:18][C:19]3[NH:23][C:22]([CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)=[N:21][C:20]=3[C:30](O)=[O:31])[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2.[CH:33]1[CH:38]=[C:37]([S:39]([OH:42])(=[O:41])=[O:40])[CH:36]=[C:35]([NH2:43])[CH:34]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl.CN(C=O)C.CN(C)C1C=CN=CC=1.CO.C(OCC)(=O)C.O>[C:7]12([CH2:17][CH2:18][C:19]3[NH:23][C:22]([CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)=[N:21][C:20]=3[C:30]([NH:43][C:35]3[CH:36]=[C:37]([S:39]([OH:42])(=[O:40])=[O:41])[CH:38]=[CH:33][CH:34]=3)=[O:31])[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2

Participants

11

Reactant 4

HCID 84743-Aminobenzenesulfonic acidHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 18405518HCID 18405518, compound

Product 1

HCID 18405376HCID 18405376, compoundYield 41%

Reagents, catalysts & solvents 6

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Oxalyl chloride (147 μl, 1.69 mmol) was added to an ice cooled suspension of 5-(2-adamantan-1-yl-ethyl)-2-cyclohexyl-1H-imidazole-4-carboxylic acid (Example 252) (500 mg, 1.40 mmol) in DCM (8 ml), followed by two drops of DMF. The mixture was stirred at room temperature for 1 h, then the solvent was evaporated. The residue was susupended in THF (8 ml), and tretaed sequentially with metanilic acid (346 mg, 2.00 mmol), N,N-diisopropylethylamine (348 μl, 2.00 mmol) and 4-dimethylaminopyridine (DMAP) (cat). The suspension was stirred at room temperature for 120 h. Water (30 ml), ethyl acetate (30 ml) and methanol (2 ml) were added and the mixture was stirred for 1 h. The solid was filtered and dried to afford the title compound (294 mg, 41%). 1H NMR (300 MHz, d6-DMSO) 10.10 (1H, br s), 7.92 (1H, br s), 7.67 (1H, m), 7.34 (2H, m), 2.98-2.86 (3H, m), 2.02-1.34 (27H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 57.87; H, 7.73; N, 7.74%. C35H54N5O9S.1.0 mol H2O requires: C, 57.99; H, 7.79; N, 7.73%.

Workup

  1. temperaturecooled
  2. customthe solvent was evaporated
  3. stirringThe suspension was stirred at room temperature for 120 h
  4. stirringthe mixture was stirred for 1 h
  5. filtrationThe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-1a8e5ba72f794b96a5ca4da691d09de4
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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