Hydrochloric Acid → HCID 59465872, compound

HRID 1876695Notes

Reaction equation

HRID 1876695 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([S:20](=[O:28])(=[O:27])[NH:21][C:22]3[S:23][CH:24]=[CH:25][N:26]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+].Cl>C(Cl)Cl>[NH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH:21][C:22]3[S:23][CH:24]=[CH:25][N:26]=3)(=[O:28])=[O:27])=[CH:16][CH:15]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 59466300HCID 59466300, compound

Product 1

HCID 59465872HCID 59465872, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared using general procedure 28, method A. A mixture of tert-butyl-1-(4-(N-thiazol-2-ylsulfamoyl)phenyl)piperidin-4-ylcarbamate (657 mg, 1.5 mmol), TFA (1.5 mL) and CH2Cl2 (10 mL) was stirred at RT under an N2 atmosphere for 2.5 h. The reaction was poured into saturated NaHCO3 solution (50 mL) and acidified to pH 3-4 with a 1 M HCl solution. The mixture was then extracted with CH2Cl2 (3×50 mL). Since LCMS analysis showed that the product was still in the aqueous layer, it was neutralized with saturated NaHCO3 resulting in precipitation of a white solid which was filtered, washed with MeOH, and dried under vacuum to obtain 4-(4-aminopiperidin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide (200 mg, 38% over 2 steps). 1H NMR (400 MHz, DMSO-d6) δ 7.57-7.45 (m, 4H), 6.94-6.89 (m, 3H), 6.44 (d, J=3.9 Hz, 1H), 3.83 (d, J=13.5 Hz, 2H), 3.20-3.14 (m, 1H), 2.83 (t, J=11.8 Hz, 2H), 1.84 (d, J=9.3 Hz, 2H), 1.51-1.41 (m, 2H).

Workup

  1. customPrepared
  2. extractionThe mixture was then extracted with CH2Cl2 (3×50 mL)
  3. customwas neutralized with saturated NaHCO3 resulting in precipitation of a white solid which
  4. filtrationwas filtered
  5. washwashed with MeOH
  6. customdried under vacuum

Sources & evidence

ORD record
ord-4e06c7f843ee4421abaae968b684e30b
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

Loading…