Hydrochloric Acid → HCID 178480244, compound

HRID 1455540Notes

Reaction equation

HRID 1455540 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([S:17]([C:20]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH:23]=[CH:22][CH:21]=4)(=[O:19])=[O:18])[CH:15]=3)[NH:10][N:9]=2)[CH2:4][CH2:3]1.[ClH:30].O.OOS([O-])=O.[K+]>CO>[ClH:30].[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([S:17]([C:20]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH:23]=[CH:22][CH:21]=4)(=[O:18])=[O:19])[CH:15]=3)[NH:10][N:9]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 178480243HCID 178480243, compound

Product 1

HCID 178480244HCID 178480244, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(1-methylpiperidin-4-yl)-5-(1-naphthylsulfonyl)-1H-indazole (0.16 g, 0.44 mmol) in CH3OH was treated with concentrated HCl (0.05 mL) and the resulting solution was concentrated to dryness. The resultant residue was redissolved in CH3OH (8.8 mL), treated sequentially with water (8.8 mL) and Oxone®1 (0.54 g, 0.88 mmol), stirred at room temperature for 20 min and concentrated in vacuo. This residue was dissolved in DMSO and purified by Gilson reverse phase HPLC. The purified material was treated with anhydrous HCl in ether and evaporated to dryness to afford the title compound as a yellow solid, 125 mg (64% yield), identified by HNMR and mass spectral analyses. MS (ES+) m/e 406 (MH+). 1Oxone® is potassium peroxymonosulfate, manufactured by Aldrich Chemical Co.

Workup

  1. concentrationthe resulting solution was concentrated to dryness
  2. dissolutionThe resultant residue was redissolved in CH3OH (8.8 mL)
  3. concentrationconcentrated in vacuo
  4. dissolutionThis residue was dissolved in DMSO
  5. custompurified by Gilson reverse phase HPLC
  6. additionThe purified material was treated with anhydrous HCl in ether
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-9cdf7206611e4fcb9c7b85ad5eb28577
Source dataset
uspto-grants-2009_01
Patent number
US07482461B2

Reaction notes

Loading…