TBAF tetrahydrofuran → HCID 71735796, compound

HRID 717085Notes

Reaction equation

HRID 717085 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[CH:19][C:18]([C:21]3[NH:22][C:23](=[O:32])[C:24]4[C:29]([CH:30]=3)=[C:28]([CH3:31])[CH:27]=[CH:26][CH:25]=4)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>C1COCC1.CCOC(C)=O>[OH:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[CH:19][C:18]([C:21]3[NH:22][C:23](=[O:32])[C:24]4[C:29]([CH:30]=3)=[C:28]([CH3:31])[CH:27]=[CH:26][CH:25]=4)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 123555131HCID 123555131, compound

Product 1

HCID 71735796HCID 71735796, compoundYield 16.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(6-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-piperazin-1-yl}-pyridin-3-yl)-5-methyl-2H-isoquinolin-1-one (214 mg, 0.45 mmol) in THF (1.5 mL) at 5° C. was added 1M TBAF/THF (0.58 mL, 0.58 mmol) dropwise. The reaction mixture was allowed to warm to RT and stirred for 1 h. The reaction mixture was diluted with EtOAc (10 mL) and washed with water and brine. The organic layer was concentrated in vacuo and purified by reverse phase preparative HPLC-MS to obtain 3-{6-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-pyridin-3-yl}-5-methyl-2H-isoquinolin-1-one as a yellow solid (27 mg, 16%).

Workup

  1. washwashed with water and brine
  2. concentrationThe organic layer was concentrated in vacuo
  3. custompurified by reverse phase preparative HPLC-MS

Sources & evidence

ORD record
ord-9782f74d48c54ba8bc014f7e3c32bfd8
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

Loading…