Hydrochloric Acid → HCID 16656820, compound

HRID 578812Notes

Reaction equation

HRID 578812 reaction equation
C[O:2][C:3]([C:5]1[S:6][CH:7]=[C:8]2[C:13]=1[C:12](=[O:14])[N:11]([C:15]1[CH:20]=[C:19]([S:21]([N:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:27][CH2:26][CH2:25]3)(=[O:23])=[O:22])[CH:18]=[CH:17][C:16]=1[Cl:34])[C:10](=[O:35])[NH:9]2)=O.[H-].C([Al+]CC(C)C)C(C)C.C(OCC)(=O)C.Cl>O1CCCC1>[OH:2][CH2:3][C:5]1[S:6][CH:7]=[C:8]2[C:13]=1[C:12](=[O:14])[N:11]([C:15]1[CH:20]=[C:19]([S:21]([N:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:27][CH2:26][CH2:25]3)(=[O:22])=[O:23])[CH:18]=[CH:17][C:16]=1[Cl:34])[C:10](=[O:35])[NH:9]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 16657782HCID 16657782, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 16656820HCID 16656820, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-methoxycarbonyl-3-[2-chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)phenyl]thieno[3,4-d]-pyrimidine-2,4(1H,3H)-dione (0.2 g) in tetrahydrofuran (4 mL) was added diisobutylaluminum hydride (1.01 mol/L toluene solution, 1.5 mL) under ice-cooling, and the mixture was stirred for 1 hour. To the reaction mixture was added ethyl acetate, and the mixture was stirred for 10minutes. To the mixture was added 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1) to give the title compound (0.11 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 10minutes
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-27ce231a92534f92ac977519de702c46
Source dataset
uspto-grants-2015_05
Patent number
US09040693B2

Reaction notes

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