Trifluoroacetic acid → 8-Azetidin-3-ylmethyl-2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine

HRID 1923229Notes

Reaction equation

HRID 1923229 reaction equation
[CH3:1][N:2]1[C:10]([CH2:11][CH:12]2[CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]2)=[N:9][C:8]2[C:3]1=[N:4][C:5]([N:29]1[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[N:31]=[C:30]1[CH2:38][CH3:39])=[N:6][C:7]=2[N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:14]1[CH2:13][CH:12]([CH2:11][C:10]2[N:2]([CH3:1])[C:3]3[C:8]([N:9]=2)=[C:7]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:6]=[C:5]([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:4]=3)[CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596056563-[2-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethyl]azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 596052818-Azetidin-3-ylmethyl-2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-((9-methyl-2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)methyl)azetidine-1-carboxylate (0.64 g, 1.2 mmol) in DCM (10 mL) was added trifluoroacetic acid (1.0 mL, 13 mmol) The reaction mixture was then stirred at room temperature for 1 hour. The reaction mixture was then evaporated to dryness. The residue was then re-dissolved in MeOH and neutralized by adding a 2M NH3 in MeOH. The solution was then concentrated and purified by flash chromatography using a KP-NH2 column (0-10% MeOH in DCM) to give 530. LCMS m/z: 433.2 (MH+)

Workup

  1. customThe reaction mixture was then evaporated to dryness
  2. dissolutionThe residue was then re-dissolved in MeOH
  3. additionby adding a 2M NH3 in MeOH
  4. concentrationThe solution was then concentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-9ee4cda1e2974fd089112e4a370af5d3
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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