Acetonitrile → HCID 59496719, compound

HRID 449427Notes

Reaction equation

HRID 449427 reaction equation
[C:1](Cl)(=[O:12])[O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.Cl.[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[C:26]([C:28]3[CH:37]=[C:36]4[C:31]([CH2:32][CH2:33][NH:34][CH2:35]4)=[CH:30][CH:29]=3)[N:25]=[C:24]([NH2:38])[N:23]=2)[CH2:18][CH2:17]1.C(N(CC)CC)C.C(#N)C>O>[NH2:38][C:24]1[N:25]=[C:26]([C:28]2[CH:37]=[C:36]3[C:31]([CH2:32][CH2:33][N:34]([C:1]([O:2][C:3]4[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=4)=[O:12])[CH2:35]3)=[CH:30][CH:29]=2)[CH:27]=[C:22]([N:19]2[CH2:18][CH2:17][N:16]([CH3:15])[CH2:21][CH2:20]2)[N:23]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 675414894-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt

Product 1

HCID 59496719HCID 59496719, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Nitrophenyl carbonochloridate (0.14 g, 0.69 mmol) was added to 4-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt (0.30 g, 0.69 mmol) and triethylamine (0.38 mL, 2.8 mmol) in acetonitrile (8.0 mL, 150 mmol) at 0° C. After 1 h., the mixture was diluted with water, and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with MeOH in dicloromethane (0-10%) to afford the desired product (0.32 g, 94%). Analytic LCMS (M+H)+: m/z=490.2.

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on a silica gel column with MeOH in dicloromethane (0-10%)

Sources & evidence

ORD record
ord-61a081e92d4c42de91de4a5857268dff
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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