Hydrochloric Acid → HCID 85064118, compound

HRID 351053Notes

Reaction equation

HRID 351053 reaction equation
Cl.[NH2:2][OH:3].C([O-])(O)=O.[Na+].[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][S:17]([C:20]2[CH:21]=[C:22]([CH:26]=[CH:27][C:28](Cl)=[O:29])[CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH:10]=1.Cl>O1CCCC1.O>[OH:3][NH:2][C:28](=[O:29])[CH:27]=[CH:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([S:17](=[O:19])(=[O:18])[NH:16][CH2:15][C:11]2[CH:10]=[N:9][CH:14]=[CH:13][CH:12]=2)[CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 73989424HCID 73989424, compound

Product 1

HCID 85064118HCID 85064118, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of hydroxylamine hydrochloride (0.31 g, 4.40 mmol) in tetrahydrofuran (5 ml) a saturated NaHCO3 solution (6.8 ml) was added and the resultant mixture was stirred at ambient temperature for 10 min. To the reaction mixture a solution of crude 3-{3-[(pyridin-3-ylmethyl)-sulfamoyl]-phenyl}-acryloyl chloride (16b) (0.29 g, 0.86 mmol) in tetrahydrofuran (5 ml) was added and the mixture was stirred at ambient temperature for one hour. The reaction mixture was poured into water, the obtained solution was acidified with 2N HCl to pH˜5 of the reaction medium and extracted with ethyl acetate. The organic layer was washed successively with water and saturated NaCl, then the solvent was removed. The residue was washed with hot ethyl acetate and methanol affording the title compound (0.12 g, 37%). M.p. 191° C. 1H NMR (DMSO-d6, HMDSO) δ: 4.05 (2H, d, J=6.4 Hz); 6.56 (1H, d, J=16.0 Hz); 7.16–8.05 (7H, m); 8.16–8.49 (3H, m); 9.12 (1H, br s); 10.80 (1H, br s). HPLC analysis on Symmetry C18 column: impurities 8% (column size 3.9×150 mm; mobile phase acetonitrile—0.1M phosphate buffer (pH 2.5), 10:90; sample concentration 0.4 mg/ml; flow rate 1.3 ml/min; detector UV 270 nm). Anal. Calcd for C15H15N3O4S containing 0.5% of inorganic impurities, %: C, 53.77; H, 4.51; N, 12.54. Found, %: C, 53.72; H, 4.33; N, 12.41.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated NaCl
  4. customthe solvent was removed
  5. washThe residue was washed with hot ethyl acetate and methanol affording the title compound (0.12 g, 37%)

Sources & evidence

ORD record
ord-27a01297c4304bf5ac0ccb90955aea87
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Reaction notes

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