Hydrochloric Acid → HCID 66906140, compound

HRID 539564Notes

Reaction equation

HRID 539564 reaction equation
[CH3:1][N:2]([CH3:23])[C@H:3]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[N:12][CH:11]=[CH:10]2)=[O:5].[ClH:24]>C(Cl)Cl>[ClH:24].[ClH:24].[CH3:1][N:2]([CH3:23])[C@H:3]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[N:12][CH:11]=[CH:10]2)=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 44198503HCID 44198503, compound

Product 1

HCID 66906140HCID 66906140, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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. customthe solvents were evaporated

Sources & evidence

ORD record
ord-fff36958879b4b16b932de7c518ac570
Source dataset
uspto-grants-2014_10
Patent number
US08871757B2

Reaction notes

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