Sodium Hydroxide → HCID 59465606, compound

HRID 1876685Notes

Reaction equation

HRID 1876685 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[CH2:21][CH2:20][N:19](C(=O)C(F)(F)F)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)(=[O:9])=[O:8].[OH-].[Na+]>CC(O)=O>[NH:19]1[CH2:18][CH2:17][CH:16]([C:13]2[CH:12]=[CH:11][C:10]([S:7]([NH:6][C:2]3[S:1][CH:5]=[CH:4][N:3]=3)(=[O:8])=[O:9])=[CH:15][CH:14]=2)[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59465844HCID 59465844, compound

Product 1

HCID 59465606HCID 59465606, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared using general procedure 16. To N-(thiazol-2-yl)-4-(1-(2,2,2-trifluoroacetyl)piperidin-4-yl)benzenesulfonamide (1.5 g, 3.57 mmol) was added a solution of NaOH (1.43 g in 25 ml of H2O). The reaction was stirred at RT for 30 minutes. The pH was adjusted to 10 with HOAc, and the product crashed out as a pink solid which was then filtered, azeotroped with acetonitrile and dried to give 4-(piperidin-4-yl)-N-(thiazol-2-yl)benzenesulfonamide (1 g, 87% yield). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=324.3; tR=0.46 min.

Workup

  1. customPrepared
  2. filtrationwas then filtered
  3. customazeotroped with acetonitrile
  4. customdried

Sources & evidence

ORD record
ord-42474d0d9d8e4d6b99d3e19a8214d6e6
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

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