Hydrochloric Acid → 2-(2-Isopropylbenzoimidazol-1-yl)-8-(3-methoxypiperidin-3-yl)-9-methyl-6-morpholin-4-yl-9H-purine

HRID 1923317Notes

Reaction equation

HRID 1923317 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:16]2[N:17]([CH3:43])[C:18]3[C:23]([N:24]=2)=[C:22]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[N:21]=[C:20]([N:31]2[C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=4[N:33]=[C:32]2[CH:40]([CH3:42])[CH3:41])[N:19]=3)([O:14][CH3:15])[CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1.CO>[CH:40]([C:32]1[N:31]([C:20]2[N:19]=[C:18]3[C:23]([N:24]=[C:16]([C:10]4([O:14][CH3:15])[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]4)[N:17]3[CH3:43])=[C:22]([N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)[N:21]=2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:33]=1)([CH3:42])[CH3:41]

Participants

6

Reactant 2

HCID 313Hydrochloric Acid2×HCID 596052973-[2-(2-Isopropylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]-3-methoxypiperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 596052822-(2-Isopropylbenzoimidazol-1-yl)-8-(3-methoxypiperidin-3-yl)-9-methyl-6-morpholin-4-yl-9H-purineYield 89.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-[2-(2-isopropylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]-3-methoxypiperidine-1-carboxylic acid tert-butyl ester (2.47 g, 4.18 mmol) in DCM (100 mL) was added 4M HCl in dioxane (10 mL). The resulting mixture was allowed to stir for 2 h at r.t. before further 1.25M HCl in MeOH (20 mL) was added. The resulting mixture was allowed to stir for 1.5 h then concentrated in vacuo. The resulting residue was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH affording 2-(2-Isopropylbenzoimidazol-1-yl)-8-(3-methoxypiperidin-3-yl)-9-methyl-6-morpholin-4-yl-9H-purine (1.83 g, 89%). LCMS (method H): RT 2.12 min [M+H]+ 491.4

Workup

  1. additionwas added
  2. concentrationthen concentrated in vacuo
  3. washwas washed with MeOH
  4. washthe product eluted with 2M NH3/MeOH

Sources & evidence

ORD record
ord-1ae58bdadd0a4870b6b9cd04b4f60a8c
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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