Diethyl Sulfate → HCID 13137009, compound

HRID 851231Notes

Reaction equation

HRID 851231 reaction equation
Br.Br.[CH2:3]([N:5]([CH2:26][CH3:27])[CH:6]([CH3:25])[CH2:7][N:8]1[CH2:13][CH2:12][C:11]2[C:14]3[CH:22]=[C:21]([OH:23])[C:20]([OH:24])=[CH:19][C:15]=3[O:16][C:17](=[O:18])[C:10]=2[CH2:9]1)[CH3:4].C(=O)([O-])[O-].[K+].[K+].S(OCC)(O[CH2:38][CH3:39])(=O)=O.[C:43]1(N)C(F)=C(F)C(F)=C(N)[C:44]=1F.[ClH:55].Cl>C(O)C>[ClH:55].[ClH:55].[CH2:26]([N:5]([CH2:3][CH3:4])[CH:6]([CH3:25])[CH2:7][N:8]1[CH2:13][CH2:12][C:11]2[C:14]3[CH:22]=[C:21]([O:23][CH2:38][CH3:39])[C:20]([O:24][CH2:43][CH3:44])=[CH:19][C:15]=3[O:16][C:17](=[O:18])[C:10]=2[CH2:9]1)[CH3:27]

Participants

6

Reactant 4

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 13137007HCID 13137007, compound

Product 1

HCID 13137009HCID 13137009, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared by the method described in Example 37 from 3-[2-(diethylamino)propyl]-1,2,3,4-tetrahydro-8,9-dihydroxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one dihydrobromide (17.0 g, 0.034 moles), potassium carbonate (27.6 g, 0.20 moles), and diethyl sulfate (20.0 g, 0.13 moles). The crude free base product is converted to the dihydrochloride in absolute ethanol. A second recrystallization from ethanol yielded the final product (1.8 g), mp 148°-152° C.

Workup

  1. customPrepared by the method
  2. customA second recrystallization from ethanol

Sources & evidence

ORD record
ord-5098c1c0d8c141bd89e235addf461b08
Source dataset
uspto-grants-1983_05
Patent number
US04382939

Reaction notes

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