Trifluoroacetic acid → HCID 59605917, compound

HRID 1923363Notes

Reaction equation

HRID 1923363 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[N:17]([CH3:42])[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[CH2:40][CH3:41])[N:19]=3)([O:14][CH3:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:40]([C:32]1[N:31]([C:20]2[N:19]=[C:18]3[C:23]([N:24]=[C:16]([C:11]4([O:14][CH3:15])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[N:17]3[CH3:42])=[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)[CH3:41]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59605595HCID 59605595, compound

Product 1

HCID 59605917HCID 59605917, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]-4-methoxypiperidine-1-carboxylic acid tert-butyl ester (915 mg, 1.59 mmol) in DCM (15 mL) was added TFA (3 mL) and the resulting mixture allowed to stir at r.t. for 2 h. The reaction mixture was concentrated in vacuo and the resulting residue loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH affording 2-(2-Ethylbenzoimidazol-1-yl)-8-(4-methoxypiperidin-4-yl)-9-methyl-6-morpholin-4-yl-9H-purine (775 mg, quant.). LCMS (method H): RT 1.95 min, [M+H]+ 477.3

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwas washed with MeOH
  3. washthe product eluted with 2M NH3/MeOH

Sources & evidence

ORD record
ord-9d9444483f7e4f0b8c3fa269c6d10cc2
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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