Hydrochloric Acid → 3-[2-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]piperidin-3-ol dihydrochloride

HRID 1946149Notes

Reaction equation

HRID 1946149 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:15]2[N:16]([CH3:41])[C:17]3[C:22]([N:23]=2)=[C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:20]=[C:19]([N:30]2[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[N:32]=[C:31]2[CH2:39][CH3:40])[N:18]=3)([OH:14])[CH2:9]1)=O)(C)(C)C.[ClH:42].CCOCC>C(Cl)Cl.CO.O1CCOCC1>[ClH:42].[ClH:42].[CH2:39]([C:31]1[N:30]([C:19]2[N:18]=[C:17]3[C:22]([N:23]=[C:15]([C:10]4([OH:14])[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]4)[N:16]3[CH3:41])=[C:21]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[N:20]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=1)[CH3:40]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 596057583-[2-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]-3-hydroxypiperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 674921803-[2-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]piperidin-3-ol dihydrochlorideYield 92%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-[2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]-3-hydroxypiperidine-1-carboxylic acid tert-butyl ester (1.0 g, 1.78 mmol) in DCM (5 mL) and MeOH (1 mL) was added 4M HCl in dioxane (5 mL). The resulting mixture was allowed to stir for 2 h at r.t. before Et2O was added. The resulting precipitate was collected by filtration, washed with Et2O and dried in vacuo affording 3-[2-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]piperidin-3-ol dihydrochloride (870 mg, 92%). LCMS (method H): RT 1.84 min [M+H]+ 463.3

Workup

  1. additionwas added
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with Et2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-b40977fa31b84b4fabab7e89a181f794
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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