1,4-Dioxane hydrochloride → HCID 117992611, compound

HRID 717114Notes

Reaction equation

HRID 717114 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[NH:22][C:23](=[O:33])[C:24]4[C:29]([CH:30]=3)=[C:28]([C:31]#[CH:32])[CH:27]=[CH:26][CH:25]=4)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[C:31]([C:28]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:29]=1[CH:30]=[C:21]([C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:16][CH:17]=1)[NH:22][C:23]2=[O:33])#[CH:32]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 89812915HCID 89812915, compound

Product 1

HCID 117992611HCID 117992611, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[4-(5-Ethynyl-1-oxo-1,2-dihydroisoquinolin-3-yl)benzyl]piperazine-1-carboxylic acid tert-butyl ester (60.3 mg, 0.136 mmol) and 4M HCl/dioxane (3 mL) in CH2Cl2 (3 mL) were stirred at RT for 2 h. The reaction mixture was concentrated in vacuo and the crude material was purified by reverse phase preparative HPLC-MS to obtain 5-ethynyl-3-(4-piperazin-1-ylmethylphenyl)-2H-isoquinolin-1-one as an off-white solid (16.0 mg, 34%).

Workup

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

Sources & evidence

ORD record
ord-4b28cf7f869441148e7c1bd418974d0c
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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