Trifluoroacetic acid → HCID 58117088, compound

HRID 2066538Notes

Reaction equation

HRID 2066538 reaction equation
C(O[C:6]([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][N:12]([CH2:16][C:17]3[S:25][C:24]4[C:23]([N:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)=[N:22][C:21]([Cl:32])=[N:20][C:19]=4[CH:18]=3)[CH2:13]2)[CH2:9]1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O.C[Si]([N:44]=C=O)(C)C>C(Cl)Cl>[Cl:32][C:21]1[N:22]=[C:23]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:24]2[S:25][C:17]([CH2:16][N:12]3[CH2:13][CH:14]4[CH2:15][N:8]([C:6]([NH2:44])=[O:7])[CH2:9][CH:10]4[CH2:11]3)=[CH:18][C:19]=2[N:20]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 70696Trimethylsilyl isocyanateHCID 581170715-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester

Product 1

HCID 58117088HCID 58117088, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester (250 mg, 0.52 mmol) in DCM (4.5 mL) was added TFA (0.5 mL). The reaction mixture stirred at RT for 1 h, then loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH then eluted with 2 M NH3 in MeOH, and concentrated in vacuo. The resultant residue was dissolved in DCM (5 mL) and trimethylsilyl isocyanate (139 μL, 1.0 mmol) was added. The reaction mixture was stirred at RT for 1 h, then partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic layer was separated and washed with brine, then dried (Na2SO4) and concentrated in vacuo to give the title compound as a colourless oil (185 mg, 84%).

Workup

  1. washThe cartridge was washed with MeOH
  2. washthen eluted with 2 M NH3 in MeOH
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resultant residue was dissolved in DCM (5 mL)
  5. stirringThe reaction mixture was stirred at RT for 1 h
  6. custompartitioned between DCM
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5cb9ed1fbc1d4a6b8a546628435cb2bc
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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