Hydrochloric Acid → HCID 23114891, compound

HRID 2080523Notes

Reaction equation

HRID 2080523 reaction equation
[Cl:1][C:2]1[C:3]([CH:27]([S:36]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=2)(=[O:38])=[O:37])[C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])=[CH:4][C:5]([NH:8][S:9]([CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)(=[O:11])=[O:10])=[N:6][CH:7]=1.Cl.C(=O)(O)[O-].[Na+]>C(O)C>[Cl:1][C:2]1[C:3]([CH:27]([S:36]([C:39]2[CH:40]=[CH:41][C:42]([Cl:45])=[CH:43][CH:44]=2)(=[O:38])=[O:37])[C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])=[CH:4][C:5]([NH:8][S:9]([CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)(=[O:10])=[O:11])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 23114677HCID 23114677, compound

Product 1

HCID 23114891HCID 23114891, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol (5 ml) solution of t-butyl 4-[2-[[[5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amino]sulfonyl]ethyl]piperazine-1-carboxylate (72 mg, 0.102 mmol) was added concentrated hydrochloric acid (1 ml). The resulting mixture was stirred at room temperature for 2 days, followed by concentration under reduced pressure. To the residue thus obtained was added a saturated aqueous solution of sodium bicarbonate. The resulting mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was washed with ether to give the title compound (23 mg, 0.038 mmol, 37%) as a white powder.

Workup

  1. concentrationfollowed by concentration under reduced pressure
  2. customTo the residue thus obtained
  3. extractionThe resulting mixture was extracted with methylene chloride
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe residue thus obtained
  8. washwas washed with ether

Sources & evidence

ORD record
ord-781bfddd2ad044b481158a914aa8df36
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

Loading…