Acetic Acid → HCID 44198503, compound

HRID 539563Notes

Reaction equation

HRID 539563 reaction equation
Cl.Cl.N[C@H:4]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[N:13][CH:12]=[CH:11]2)=[O:6].C=O.[CH3:26]C(O)=O.[BH3-][C:31]#[N:32].[Na+]>CO>[CH3:26][N:32]([CH3:31])[C@H:4]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[N:13][CH:12]=[CH:11]2)=[O:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66906141HCID 66906141, compound

Product 1

HCID 44198503HCID 44198503, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (R)-2-amino-N-(isoquinolin-6-yl)-2-phenylacetamide dihydrochloride (E2) in MeOH was added CH2O (37%), AcOH and NaCNBH3. After stirring for 1.5 hours the solution was poured into NaHCO3(sat) and extracted with EtOAc, dried (Na2SO4), filtered and concentrated. Column chromatography Hexanes/EtOAc gave pure (R)-2-(dimethylamino)-N-(isoquinolin-6-yl)-2-phenylacetamide. To (R)-2-(dimethylamino)-N-(isoquinolin-6-yl)-2-phenylacetamide was added CH2Cl2 and HCl (4N in dioxane) and the solvents were evaporated to give pure (R)-2-(dimethylamino)-N-(isoquinolin-6-yl)-2-phenylacetamide dihydrochloride (E3).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1ebe883917934c34a19fceebbd821af7
Source dataset
uspto-grants-2014_10
Patent number
US08871757B2

Reaction notes

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