Trifluoroacetic acid → HCID 59605600, compound

HRID 1946164Notes

Reaction equation

HRID 1946164 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([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])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:39]([C:31]1[N:30]([C:19]2[N:18]=[C:17]3[C:22]([N:23]=[C:15]([C:11]4([OH:14])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]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

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59605258HCID 59605258, compound

Product 1

HCID 59605600HCID 59605600, compoundYield 102.9%

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-hydroxypiperidine-1-carboxylic acid tert-butyl ester (1.3 g, 2.31 mmol) in DCM (10 mL) was added TFA (2 mL) and the resulting mixture allowed to stir at r.t. for 3 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 4-[2-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]piperidin-4-ol (1.1 g, quant.). LCMS (method H): RT 1.79 min, [M+H]+ 463.3

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-628bc7b3a72a496f963b8d9a6feef392
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

Loading…