HCID 178454061, compound → HCID 178508358, compound

HRID 1366742Notes

Reaction equation

HRID 1366742 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21]([NH2:25])=[N:20][CH:19]=[CH:18]3)[CH2:10][CH2:9]1)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[NH2:7][C@@H:8]1[CH2:9][CH2:10][C@H:11]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21]([NH2:25])=[N:20][CH:19]=[CH:18]3)[CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 178454061HCID 178454061, compound

Product 1

HCID 178508358HCID 178508358, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of cis-[4-(1-aminoisoquinolin-6-yloxy)cyclohexyl]carbamic acid tert-butyl ester (14 mg) in dichloromethane (900 μl) and trifluoroacetic acid (100 μl) was stirred at ambient temperature for 3 h. The mixture was concentrated in vacuo then purified by prep-HPLC to give gave cis-6-(4-aminocyclohexyloxy)isoquinolin-1-ylamine (8.1 mg), EI-MS: m/z=258.5 [M+H]+. 1H NMR (methanol D4) δ1.55-1.80 (6H, m), 2.05-2.15 (2H, m), 2.75-2.85 (1H, m), 4.65-4.75 (1H, obscured broad s), 6.88 (1H, d), 7.08-7.15 (2H, m), 7.64 (1H, d), 7.99 (1H, d).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthen purified by prep-HPLC
  3. customto give

Sources & evidence

ORD record
ord-d983351a6b604e99a7b223f0482b984d
Source dataset
uspto-grants-2011_02
Patent number
US07893088B2

Reaction notes

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