Potassium Carbonate → HCID 178454082, compound

HRID 1366746Notes

Reaction equation

HRID 1366746 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([NH:14][C@@H:15]1[CH2:20][CH2:19][C@H:18](OS(C)(=O)=O)[CH2:17][CH2:16]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[SH:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[C:33]([NH:37][C:38](=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[N:32][CH:31]=[CH:30]2>CC(N(C)C)=O>[C:7]([O:11][C:12](=[O:13])[NH:14][C@H:15]1[CH2:16][CH2:17][C@H:18]([S:26][C:27]2[CH:28]=[C:29]3[C:34](=[CH:35][CH:36]=2)[C:33]([NH:37][C:38](=[O:45])[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[N:32][CH:31]=[CH:30]3)[CH2:19][CH2:20]1)([CH3:8])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 136378996N-(6-mercaptoisoquinolin-1-yl)benzamideHCID 178454080HCID 178454080, compound

Product 1

HCID 178454082HCID 178454082, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

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. customThe mixture was irradiated in a microwave at 120° 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-84661a133a7544e1b99963d45b6b7d38
Source dataset
uspto-grants-2011_02
Patent number
US07893088B2

Reaction notes

Loading…