HCID 11396572, compound → HCID 57732795, compound

HRID 1806208Notes

Reaction equation

HRID 1806208 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[CH:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2]>C1COCC1.O=[Mn]=O>[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([CH:27]=[O:28])=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2]

Participants

4

Reactant 1

HCID 11396572HCID 11396572, compound

Product 1

HCID 57732795HCID 57732795, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-[4-(hydroxymethyl)phenyl]-1H-indole-7-carboxamide (25 mg, 0.058 mmol) in THF (5 mL), MnO2 (160.0 mg, 1.73 mmol) was added at ambient temperature. The resulting suspension was stirred overnight, filtered through celite, and the solid rinsed with THF (3×10 mL). The filtrate was concentrated to give the title compound (15 mg, 58%) which was used in the next step without purification.

Workup

  1. filtrationfiltered through celite
  2. washthe solid rinsed with THF (3×10 mL)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f584e6ffb69142ae91ff2b40ab8c2a11
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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