Hydrochloric Acid → HCID 59465750, compound

HRID 1876700Notes

Reaction equation

HRID 1876700 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:20][CH2:19][CH2:18][N:17]2C(=O)C(F)(F)F)=[CH:12][CH:11]=1)(=[O:9])=[O:8].[OH-].[Na+].Cl>O>[NH:17]1[CH2:18][CH2:19][CH2:20][CH:16]1[C:13]1[CH:14]=[CH:15][C:10]([S:7]([NH:6][C:2]2[S:1][CH:5]=[CH:4][N:3]=2)(=[O:8])=[O:9])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59465996HCID 59465996, compound

Product 1

HCID 59465750HCID 59465750, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Synthesized according to general procedure 38. A solution of N-(thiazol-2-yl)-4-(1-(2,2,2-trifluoroacetyl)pyrrolidin-2-yl)benzenesulfonamide (750 mg, 1.8 mmol), NaOH (221 mg, 5.5 mmol), and H2O (2.5 mL) was stirred at RT for 1 h, then cooled to 0° C. Hydrochloric acid (0.45 mL, 5.5 mmol) was added, and the reaction was stirred at 0° C. for 20 min. The formed precipitate was filtered off and dried under vacuum to give 4-(pyrrolidin-2-yl)-N-(thiazol-2-yl)benzenesulfonamide (300 mg, 53%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=310.3; tR=0.44 min.

Workup

  1. customSynthesized
  2. filtrationThe formed precipitate was filtered off
  3. customdried under vacuum

Sources & evidence

ORD record
ord-d89320fc7e5140079d90ccdd5da25d55
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

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