Acetic Acid → 6-(Piperidin-3-ylsulfanyl)isoquinolin-1-ylamine

HRID 1435980Notes

Reaction equation

HRID 1435980 reaction equation
C(O)(=O)C.Cl.C(OC([N:13]1[CH2:18][CH2:17][CH2:16][CH:15]([S:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[C:26]([NH:30]C(=O)C2C=CC=CC=2)=[N:25][CH:24]=[CH:23]3)[CH2:14]1)=O)(C)(C)C>CO>[NH:13]1[CH2:18][CH2:17][CH2:16][CH:15]([S:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[C:26]([NH2:30])=[N:25][CH:24]=[CH:23]3)[CH2:14]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 688763833-(1-Benzoylaminoisoquinolin-6ylsulfanyl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 162225646-(Piperidin-3-ylsulfanyl)isoquinolin-1-ylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Glacial acetic acid (2 ml) and 6M hydrochloric acid (4.25 ml) were added to the 3-(1-benzoylaminoisoquinolin-6ylsulfanyl)piperidine-1-carboxylic acid tert-butyl ester (18 mg, 0.039 mmol) and the mixture was refluxed for 24 h. The mixture was then concentrated in vacuo to give a residue. The residue was loaded onto a pre-acidified SCX column using methanol and then eluted with 2M ammonia in methanol to give 6-(piperidin-3-ylsulfanyl)isoquinolin-1--ylamine which was further purified using prep-HPLC, EIMS: m/z=260.3 [M+H]+

Workup

  1. temperaturethe mixture was refluxed for 24 h
  2. concentrationThe mixture was then concentrated in vacuo
  3. customto give a residue
  4. washeluted with 2M ammonia in methanol

Sources & evidence

ORD record
ord-849a95e91dac46c9865b528ebceeb03c
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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