2,4,6-Trimethylpyridine → HCID 66581072, compound

HRID 1521826Notes

Reaction equation

HRID 1521826 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([N:9]2[C:13]3[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[S:20](=[O:23])(=[O:22])[CH2:21][C:12]=3[C:11]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N:10]2)[CH:6]=[CH:7][CH:8]=1.N1C(C)=CC(C)=CC=1C.[C:38]1([O:44][C:45](Cl)=[O:46])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1COCC1>[O:44]([C:45]([NH:2][C:3]1[CH:4]=[C:5]([N:9]2[C:13]3[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[S:20](=[O:23])(=[O:22])[CH2:21][C:12]=3[C:11]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[N:10]2)[CH:6]=[CH:7][CH:8]=1)=[O:46])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 15891Phenyl chloroformateHCID 66578975HCID 66578975, compound

Product 1

HCID 66581072HCID 66581072, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-(3-aminophenyl)-1,4-dihydrothiochromeno[4,3-c]pyrazole-3-carboxylate 5,5-dioxide hydrochloride (100 mg, 0.243 mmol) in THF (10 mL) are added 2,4,6 collidine (0.06 mL, 0.487 mmol), phenylchloroformate (0.04 mL, 0.365 mmol) then stirred at RT for 18 h. After this time, reaction mixture is concentrated under reduced pressure, diluted with water, and extracted with EtOAc. The organic layer is separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 100 mg of the title compound.

Workup

  1. customAfter this time, reaction mixture
  2. concentrationis concentrated under reduced pressure
  3. additiondiluted with water
  4. extractionextracted with EtOAc
  5. customThe organic layer is separated
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-658aef0cfe7846d1aa0340009ef3b737
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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