Benzenesulfonamide, 3-amino- → Hydrochloric Acid

HRID 855636Notes

Reaction equation

HRID 855636 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][N:6]1[C:14]([CH3:15])=[C:13]2[C:8]([CH:9]=[C:10]([N:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=3)[CH3:17])[CH:11]=[CH:12]2)=[N:7]1.[NH2:28][C:29]1[CH:30]=[C:31]([S:35]([NH2:38])(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1>C(O)(C)C.Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][N:6]1[C:14]([CH3:15])=[C:13]2[C:8]([CH:9]=[C:10]([N:16]([CH3:17])[C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:28][C:29]4[CH:30]=[C:31]([S:35]([NH2:38])(=[O:36])=[O:37])[CH:32]=[CH:33][CH:34]=4)[N:19]=3)[CH:11]=[CH:12]2)=[N:7]1

Participants

6

Reactant 2

HCID 7377Benzenesulfonamide, 3-amino-HCID 21956335HCID 21956335, compound

Product 2

HCID 313Hydrochloric AcidHCID 10302148HCID 10302148, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of 2-(3-chlorobenzyl)-N-(2-chloropyrimidin-4-yl)-N,3-dimethyl-2H-indazol-6-amine (40 mg, 0.1 mmol) and 3-aminobenzenesulfonamide (17.3 mg, 0.1 mmol) in isopropanol (2 ml) was added 2 drops of conc. HCl. The mixture was heated to reflux overnight. The mixture was cooled to rt. Precipitate was collected via filtration and washed with EtOH. HCl salt of 3-({4-[[2-(3-chlorobenzyl)-3-methyl-2H-indazol-6-yl](methyl)amino]-pyrimidin-2-yl}amino)benzenesulfonamide was isolated as off-white solid. 1H NMR (400 MHz, d6DMSO+NaHCO3) δ 9.52 (br s, 1H), 8.54 (br s, 1H), 7.85 (d, J=5.9 Hz, 1H), 7.77-7.79 (m, 2H), 7.49 (s, 1H), 7.30-7.36 (m, 5H), 7.22 (br, s, 2H), 7.14 (br s, 1H), 6.90 (d, J=8.7 Hz, 1H), 5.80 (d, J=5.8 Hz, 1H), 5.64 (s, 2H), 3.48 (s, 3H), 2.62 (s, 3H). MS (ES+, m/z) 534 (M+H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. filtrationPrecipitate was collected via filtration
  4. washwashed with EtOH

Sources & evidence

ORD record
ord-013c398b0b064082b035242963bebbba
Source dataset
uspto-grants-2007_08
Patent number
US07262203B2

Reaction notes

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