4-(3-Methylsulfanyl-1-m-tolyl-1H-indazol-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester → 3-Methylsulfanyl-6-(1,2,3,6-tetrahydro-pyridin-4-yl)-1-m-tolyl-1H-indazole

HRID 68751Notes

Reaction equation

HRID 68751 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([S:30][CH3:31])=[N:19][N:20]3[C:23]3[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[CH3:31][S:30][C:18]1[C:17]2[C:21](=[CH:22][C:14]([C:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=3)=[CH:15][CH:16]=2)[N:20]([C:23]2[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=2)[N:19]=1

Participants

4

Reactant 1

HCID 674488654-(3-Methylsulfanyl-1-m-tolyl-1H-indazol-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 534941353-Methylsulfanyl-6-(1,2,3,6-tetrahydro-pyridin-4-yl)-1-m-tolyl-1H-indazole

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-(3-methylsulfanyl-1-m-tolyl-1H-indazol-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (22.5 mg, 0.052 mmol) in 4 N HCl in 1,4-dioxane (3 mL) was stirred at room temperature for 1 h, then concentrated. The resulting residue was triturated and sonicated in a mixture of MeOH (0.5 mL)/diethyl ether (5 mL). The resulting mixture was filtered to yield the title compound as a yellowish solid.

Workup

  1. concentrationconcentrated
  2. customThe resulting residue was triturated
  3. customsonicated in a mixture of MeOH (0.5 mL)/diethyl ether (5 mL)
  4. filtrationThe resulting mixture was filtered

Sources & evidence

ORD record
ord-90154f28da444a989d659fbb177a7ff0
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Reaction notes

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