Hydrochloric Acid → HCID 71737241, compound

HRID 717086Notes

Reaction equation

HRID 717086 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[NH:21][C:22](=[O:31])[C:23]4[C:28]([CH:29]=3)=[C:27]([CH3:30])[CH:26]=[CH:25][CH:24]=4)=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)(C)(C)C.Cl>C(Cl)Cl>[OH:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[NH:21][C:22](=[O:31])[C:23]4[C:28]([CH:29]=3)=[C:27]([CH3:30])[CH:26]=[CH:25][CH:24]=4)=[CH:16][CH:15]=2)[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131734156HCID 131734156, compound

Product 1

HCID 71737241HCID 71737241, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-{4-[4-(tert-butyl-diphenyl-silanyloxy)-piperidin-1-ylmethyl]-phenyl}-5-methyl-2H-isoquinolin-1-one (213 mg, 0.36 mmol) in CH2Cl2 (2 mL) was added 1.25M methanolic HCl (1 mL) and the reaction stirred at RT for 48 h. The reaction mixture was concentrated in vacuo and the crude residue purified by reverse phase preparative HPLC-MS to afford 3-[4-(4-hydroxy-piperidin-1-ylmethyl)-phenyl]-5-methyl-2H-isoquinolin-1-one as a pale yellow solid (80 mg, 64%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude residue purified by reverse phase preparative HPLC-MS

Sources & evidence

ORD record
ord-05583d8afb4f4aedbee143c8bf8ce6c0
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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