Ethyl Acetate → HCID 178486509, compound

HRID 1797933Notes

Reaction equation

HRID 1797933 reaction equation
Cl[C:2]1[N:10]=[C:9]([NH2:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=2)[CH2:22][CH2:21][NH:20]1.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>CS(C)=O.O>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=2)[CH2:22][CH2:21][N:20]1[C:2]1[N:10]=[C:9]([NH2:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 3158418HCID 3158418, compoundHCID 1785084356-chloro-1H-purin-2-amine

Product 1

HCID 178486509HCID 178486509, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 6-chloro-9H-purin-2-amine (0.25 M in dimethylsulfoxide) (800+2400 DMSO or 3200 μl) was added to 1-(2-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline followed by N,N-diisopropylethylamine (175 μl). The mixture was shaken at XX ° C. until complete then evaporated to dryness. The residue obtained was shaken at 50° C. with ethyl acetate (3 ml) and water (2 ml), for 30 minutes. The ethyl acetate layer was separated and the aqueous layer re-extracted with ethyl acetate (3 ml). The combined ethyl acetate fractions were evaporated to dryness and the residue obtained dissolved in dimethylsulfoxide (1.5 ml). 6-(1-(2-chlorophenyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)-9H-purin-2-amine was purified from the dimethylsulfoxide solution by reverse phase chromatography on a preparative LC/UV/MS system using a mass triggered fractionation. Compounds were eluted from the HPLC column (Maccel 120-10-C18 SH 10 μm 20 mmID×50 mm) at 88 ml/min with 5-95 acetonitrile/water gradient using 0.1% TFA as modifier: LCMS m/e 437 (M+1).

Workup

  1. customuntil complete then evaporated to dryness
  2. customThe residue obtained
  3. customThe ethyl acetate layer was separated
  4. extractionthe aqueous layer re-extracted with ethyl acetate (3 ml)
  5. customThe combined ethyl acetate fractions were evaporated to dryness
  6. customthe residue obtained
  7. custom6-(1-(2-chlorophenyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)-9H-purin-2-amine was purified from the dimethylsulfoxide solution by reverse phase chromatography on a preparative LC/UV/MS system
  8. washCompounds were eluted from the HPLC column (Maccel 120-10-C18 SH 10 μm 20 mmID×50 mm) at 88 ml/min with 5-95 acetonitrile/water gradient

Sources & evidence

ORD record
ord-0d69cdd778e9419cbc42a18a664f8cab
Source dataset
uspto-grants-2013_01
Patent number
US08343961B2

Reaction notes

Loading…