HCID 10150940, compound → HCID 22638609, compound

HRID 2416216Notes

Reaction equation

HRID 2416216 reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:14]3[N:15]=[C:16]([CH2:19][S:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)(=[O:22])=[O:21])[S:17][CH:18]=3)[C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1>CN(C=O)C.O=[Mn]=O>[C:23]1([S:20]([CH2:19][C:16]2[S:17][CH:18]=[C:14]([C:8]3[C:9](=[O:13])[NH:10][C:11]4[C:6]([CH:7]=3)=[CH:5][CH:4]=[C:3]([CH:2]=[O:1])[CH:12]=4)[N:15]=2)(=[O:22])=[O:21])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 10150940HCID 10150940, compound

Product 1

HCID 22638609HCID 22638609, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(hydroxymethyl)-3-(2-((phenylsulfonyl)methyl)-1,3-thiazol-4-yl)-2(1H)-quinolinone (Example 8723, 1.7 g, 4.12 mmol) in 150 mL of DMF was added 25 g of MnO2. The mixture was stirred at RT for 24 h. The solids were filtered off through Celite®. 20 mL of DMF was used to rinse the solid. The combined filtrate containing the intermediate aldehyde was stored in refrigerator until being used for the next step without further purification. MS m/z: 411.0 (M+1).

Workup

  1. filtrationThe solids were filtered off through Celite®
  2. washto rinse the solid
  3. additionThe combined filtrate containing the intermediate aldehyde
  4. customuntil being used for the next step without further purification

Sources & evidence

ORD record
ord-e9df486b2c27459195863e7007732eb1
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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