HCID 89462644, compound → HCID 89462908, compound

HRID 1473249Notes

Reaction equation

HRID 1473249 reaction equation
[OH:1][CH2:2][C:3]1[N:8]([CH3:9])[C:7](=[O:10])[C:6]2[S:11][C:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[C:5]=2[C:4]=1[C:18]1[C:19]([CH3:28])=[C:20]2[C:25](=[CH:26][CH:27]=1)[O:24][CH2:23][CH2:22][CH2:21]2>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH3:9][N:8]1[C:3]([CH:2]=[O:1])=[C:4]([C:18]2[C:19]([CH3:28])=[C:20]3[C:25](=[CH:26][CH:27]=2)[O:24][CH2:23][CH2:22][CH2:21]3)[C:5]2[C:13]3[CH2:14][CH2:15][CH2:16][CH2:17][C:12]=3[S:11][C:6]=2[C:7]1=[O:10]

Participants

4

Reactant 1

HCID 89462644HCID 89462644, compound

Product 1

HCID 89462908HCID 89462908, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 3-(hydroxymethyl)-2-methyl-4-(5-methylchroman-6-yl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-c]pyridin-1(2H)-one (60 mg, 0.15 mmol) in chloroform (15 mL) was added manganese(IV) oxide (132 mg, 1.5 mmol). The mixture was stirred at reflux for 18 h. After the reaction mixture was cooled to room temperature, the suspension was filtered through a pad of silica gel and the pad was washed with ethyl acetate (20 mL×3). The combined filtrates were concentrated to dryness to give crude title product (50 mg, 84% yield), which was used in the next step directly. LCMS (m/z) ES+=396 (M+1).

Workup

  1. temperatureat reflux for 18 h
  2. filtrationthe suspension was filtered through a pad of silica gel
  3. washthe pad was washed with ethyl acetate (20 mL×3)
  4. concentrationThe combined filtrates were concentrated to dryness

Sources & evidence

ORD record
ord-02eecdd7e6894e94ad9b0675b47fbbd6
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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