Trifluoroacetic acid → HCID 59605649, compound

HRID 1923296Notes

Reaction equation

HRID 1923296 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([CH:18]4[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]4)[N:14]3[CH3:17])=[C:10]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[N:9]=2)[C:6]2[CH:35]=[CH:36][CH:37]=[CH:38][C:5]=2[N:4]=1)[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:20]1[CH2:19][CH:18]([C:13]2[N:14]([CH3:17])[C:15]3[C:11]([N:12]=2)=[C:10]([N:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)[N:9]=[C:8]([N:7]2[C:6]4[CH:35]=[CH:36][CH:37]=[CH:38][C:5]=4[N:4]=[C:3]2[CH2:1][CH3:2])[N:16]=3)[CH2:21]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59605592HCID 59605592, compound

Product 1

HCID 59605649HCID 59605649, compoundYield 85%

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]azetidine-1-carboxylic acid tert-butyl ester 678 (325 mg, 0.63 mmol) in DCM (4 mL) was added TFA (2 mL) The resulting mixture was stirred for 2.5 h at r.t then loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH/DCM and the product eluted with 2M NH3/MeOH. The resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-20%) affording 680 as a cream foam (224 mg, 85%). LCMS (method I): RT 2.30 min, [M+H]+ 419.1. 1H NMR (CDCl3, 400 MHz): δ 8.00-8.00 (1 H, m), 7.75-7.74 (1 H, m), 7.26 (2 H, s), 4.34-4.32 (7 H, m), 3.89-3.88 (6 H, m), 3.71-3.69 (3 H, m), 3.35-3.34 (2 H, m), 1.44-1.43 (3 H, m)

Workup

  1. washwas washed with MeOH/DCM
  2. washthe product eluted with 2M NH3/MeOH
  3. customThe resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-20%)

Sources & evidence

ORD record
ord-31dc455bf4154f2ea59ccac54d6b9f7a
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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