Trifluoroacetic acid → HCID 59605562, compound

HRID 1923394Notes

Reaction equation

HRID 1923394 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:17]2[N:18]([CH3:43])[C:19]3[C:24]([N:25]=2)=[C:23]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[N:22]=[C:21]([N:32]2[C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=4[N:34]=[C:33]2[CH2:41][CH3:42])[N:20]=3)([OH:16])[CH3:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:41]([C:33]1[N:32]([C:21]2[N:20]=[C:19]3[C:24]([N:25]=[C:17]([C:14]([CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)([OH:16])[CH3:15])[N:18]3[CH3:43])=[C:23]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[N:22]=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=1)[CH3:42]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596055744-{1-[2-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]-1-hydroxyethyl}piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59605562HCID 59605562, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{1-[2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]-1-hydroxyethyl}piperidine-1-carboxylic acid tert-butyl ester (104 mg, 0.18 mmol) in DCM (1 mL) was added TFA (1 mL) and the resulting mixture stirred for 1 h. The reaction mixture was concentrated in vacuo and azeotroped with DCM affording 1-[2-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-yl]-1-piperidin-4-ylethanol. LCMS (method A): RT 1.88 min, [M+H]+ 491.2

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customazeotroped with DCM

Sources & evidence

ORD record
ord-81ed1241bcae401fa6839ea414c6f4c4
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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