Hydrochloric Acid → 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine

HRID 2182369Notes

Reaction equation

HRID 2182369 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[NH:14][N:15]=[C:16]([C:17]3[NH:21][C:20]4[CH:22]=[C:23]([CH3:27])[C:24]([CH3:26])=[CH:25][C:19]=4[N:18]=3)[C:10]=2[CH2:9]1)=O)(C)(C)C.Cl>CO.O1CCOCC1>[CH3:26][C:24]1[C:23]([CH3:27])=[CH:22][C:20]2[NH:21][C:17]([C:16]3[C:10]4[CH2:9][NH:8][CH2:13][CH2:12][C:11]=4[NH:14][N:15]=3)=[N:18][C:19]=2[CH:25]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 1363343233-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 1358045913-(5,6-dimethyl-1H-benzoimidazol-2-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridineYield 70.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester [1.014 g, Example 252(a)] in methanol (20 ml) was treated with a solution of hydrogen chloride in dioxane (5 ml, 4M). After stirring for 16 hours the reaction mixture was evaporated. The resulting beige solid was triturated with methanol to yield 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine (0.523 g) as a pale yellow solid. LC-MS (METHOD B): RT=0.63 minutes; 268 (M+H)+. (b) 3-(5-Chloro-6-methyl-1H-benzoimidazol-2-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine

Workup

  1. customwas evaporated
  2. customThe resulting beige solid was triturated with methanol

Sources & evidence

ORD record
ord-50ce1d253aca4d74803bed40ef912d32
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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