Acetic Acid → HCID 178508359, compound

HRID 1366747Notes

Reaction equation

HRID 1366747 reaction equation
C(O)(=O)C.Cl.C(OC(=O)[NH:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([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)[CH2:15][CH2:14]1)(C)(C)C>CO>[NH2:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([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)[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 178454082HCID 178454082, compound

Product 1

HCID 178508359HCID 178508359, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (160 mg) and methanesulfonic acid cis-4-tert-butoxycarbonylaminocyclohexyl ester (140 mg, 0.47 mmol) were added to a solution of N-(6-mercaptoisoquinolin-1-yl)benzamide residue in DMA (4 ml). The mixture was irradiated in a microwave at 120° C. for 600 s then concentrated in vacuo to give a residue. The residue was purified by preparative HPLC to give trans-[4-(1-benzoylaminoisoquinolin-6-ylsulfanyl)cyclohexyl]carbamic acid tert-butyl ester. Glacial acetic acid (1 ml) and 6M hydrochloric acid (2 ml) were added to the trans-[4-(1-benzoylaminoisoquinolin-6-ylsulfanyl)cyclohexyl]carbamic acid tert-butyl ester 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 cude trans-6-(4-aminocyclohexylsulfanyl)isoquinolin-1-ylamine, which was further purified using prep-HPLC (9 mg), EIMS: m/z=274.5 [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-94b45f2356e24b5e8d0bc7111add1490
Source dataset
uspto-grants-2011_02
Patent number
US07893088B2

Reaction notes

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