Hydrochloric Acid → HCID 178464661, compound

HRID 2273959Notes

Reaction equation

HRID 2273959 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:6][N:5]([C:7](=[N:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21]C(=O)C)=[CH:17][CH:16]=2)(=[O:14])=[O:13])[NH:8][CH2:9][CH3:10])[N:4]=[CH:3]1.Cl.[OH-].[Na+]>CO>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([N:11]=[C:7]([N:5]2[CH2:6][C:2]([CH3:1])([CH3:25])[CH:3]=[N:4]2)[NH:8][CH2:9][CH3:10])(=[O:14])=[O:13])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178464664HCID 178464664, compound

Product 1

HCID 178464661HCID 178464661, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

900 mg N-(4-{[(4,4-Dimethyl-4,5-dihydro-pyrazol-1-yl)-ethylamino-methylene]-sulfamoyl}-phenyl) acetamide was dissolved in 5 mL MeOH, and 5 mL of concentrated HCl was added. The mixture was stirred overnight at room temperature. The mixture was basified with 2M NaOH, and extracted twice with DCM. The combined organic layers were dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (DCM/MeOH 99:1) to give 400 mg (50%) of 4-Amino-N-[(4,4-dimethyl-4,5-dihydro-pyrazol-1-yl)-ethylamino-methylene]-benzenesulfonamide as an amorphous solid. 1H NMR (400 MHz, CDCl3) δ 1.15 (t, J=7 Hz, 3H), 1.20 (s, 6H), 3.42-3.51 (m, 2H), 3.74 (br.s., 2H), 4.00 (br.s., 2H), 6.62-6.68 (m, 2H), 6.71 (s, 1H), 6.90 (br.s., 1H), 7.67-7.73 (m, 2H).

Workup

  1. extractionextracted twice with DCM
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography (DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-32a141065ff24399b1dd8be7d2c727d9
Source dataset
uspto-grants-2015_09
Patent number
US09126942B2

Reaction notes

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