Trifluoroacetic acid → 2-(2-Ethylbenzoimidazol-1-yl)-8-(3-methoxyazetidin-3-yl)-9-methyl-6-morpholin-4-yl-9H-purine

HRID 1923332Notes

Reaction equation

HRID 1923332 reaction equation
C(OC([N:8]1[CH2:11][C:10]([C:14]2[N:15]([CH3:40])[C:16]3[C:21]([N:22]=2)=[C:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:19]=[C:18]([N:29]2[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[N:31]=[C:30]2[CH2:38][CH3:39])[N:17]=3)([O:12][CH3:13])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:38]([C:30]1[N:29]([C:18]2[N:17]=[C:16]3[C:21]([N:22]=[C:14]([C:10]4([O:12][CH3:13])[CH2:11][NH:8][CH2:9]4)[N:15]3[CH3:40])=[C:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[N:19]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=1)[CH3:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596061433-[2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]-3-methoxyazetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 596058342-(2-Ethylbenzoimidazol-1-yl)-8-(3-methoxyazetidin-3-yl)-9-methyl-6-morpholin-4-yl-9H-purineYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]-3-methoxyazetidine-1-carboxylic acid tert-butyl ester (109 mg, 0.20 mmol) in DCM (2 mL) was added TFA (1 mL) and the resulting mixture allowed to stir for 1.5 h at r.t. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with DCM and MeOH and the product eluted with 2M NH3/MeOH affording 2-(2-Ethylbenzoimidazol-1-yl)-8-(3-methoxyazetidin-3-yl)-9-methyl-6-morpholin-4-yl-9H-purine as an oil (72 mg, 80%). LCMS: (method A): RT 1.86 min [M+H]+ 449.2

Workup

  1. washwas washed with DCM and MeOH
  2. washthe product eluted with 2M NH3/MeOH

Sources & evidence

ORD record
ord-d965da2483e64ce59cb0dde01d2da540
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

Loading…