Potassium Carbonate → 3-(1-Benzoylaminoisoquinolin-6ylsulfanyl)piperidine-1-carboxylic acid tert-butyl ester

HRID 1435979Notes

Reaction equation

HRID 1435979 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH:16](OS(C)(=O)=O)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[SH:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[C:32]([NH:36][C:37](=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[N:31][CH:30]=[CH:29]2>CN(C=O)C>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([S:25][C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[C:32]([NH:36][C:37](=[O:44])[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[N:31][CH:30]=[CH:29]3)[CH2:15]1)=[O:13])([CH3:8])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 568122N-Boc-3-mesyloxypiperidineHCID 136378996N-(6-mercaptoisoquinolin-1-yl)benzamide

Product 1

HCID 688763833-(1-Benzoylaminoisoquinolin-6ylsulfanyl)piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (44 mg, 0.32 mmol) and 3-methanesulfonyloxypiperidine-1-carboxylic acid tert-butyl ester (70 mg, 0.264 mmol) were added to a solution of the above N-(6-mercaptoisoquinolin-1-yl)-benzamide residue in DMF (2 ml). The mixture was irradiated in a microwave at 160° C. for 600 s then concentrated in vacuo to give a residue. The residue was purified by preparative HPLC to give 3-(1-benzoylaminoisoquinolin-6yl-sulfanyl)piperidine-1--carboxylic acid tert-butyl ester (18 mg), EIMS: m/z=464.3 [M+H]+ and m/z=486.5 [M+Na]+.

Workup

  1. customThe mixture was irradiated in a microwave at 160° C. for 600 s
  2. concentrationthen concentrated in vacuo
  3. customto give a residue
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-9c5949ce6cd540229f6adfc1dacc76cb
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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