Formaldehyde → HCID 178484113, compound

HRID 1366762Notes

Reaction equation

HRID 1366762 reaction equation
[CH3:1][NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[NH:15][CH:14]=[CH:13]3)[CH2:5][CH2:4]1.C=O.[C:23](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.C(#N)C>[CH3:1][N:2]([CH3:23])[C@H:3]1[CH2:8][CH2:7][C@H:6]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[NH:15][CH:14]=[CH:13]3)[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178484836HCID 178484836, compound

Product 1

HCID 178484113HCID 178484113, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6342AcetonitrileSolvent

Procedure

A couple of drops of glacial acetic acid were added to a solution of trans-6(4-methylaminocyclohexyloxy)-2H-isoquinolin-1-one (Example 12; 25 mg, 92 μmol) and formaldehyde (40 μL) in acetonitrile (1 ml). The mixture was stirred for 20 minutes and then sodium triacetoxyborohydride (100 mg) was added. The mixture was stirred at ambient temperature for 16 hours then concentrated in vacuo. The residue was partitioned between chloroform/isopropanol (3:1) and aqueous sodium hydrogen carbonate. The organic layer was separated then concentrated to give a residue that was purified by prep-HPLC to give trans-6(4-dimethylaminocyclohexyloxy)-2H-isoquinolin-1-one, EI-MS: m/z=287.3 [M+H]+.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 16 hours
  2. concentrationthen concentrated in vacuo
  3. customThe residue was partitioned between chloroform/isopropanol (3:1) and aqueous sodium hydrogen carbonate
  4. customThe organic layer was separated
  5. concentrationthen concentrated
  6. customto give a residue that
  7. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-74800ce085384da9b50111bffef7a9f1
Source dataset
uspto-grants-2011_02
Patent number
US07893088B2

Reaction notes

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