Sodium Hydroxide → HCID 11502814, compound

HRID 2267528Notes

Reaction equation

HRID 2267528 reaction equation
[CH:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:27]([NH2:29])=[O:28])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])=[CH2:2].[OH-:30].[Na+]>CS(C)=O>[OH:30][CH2:2][CH2:1][S:3]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:27]([NH2:29])=[O:28])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:11]1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59003347HCID 59003347, compound

Product 1

HCID 11502814HCID 11502814, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 3-[1-(ethenylsulfonyl)-4-piperidinyl]-5-phenyl-1H-indole-7-carboxamide (26 mg, 0.063 mmol) and aqueous 6M NaOH (0.2 mL) in DMSO was heated to 80° C. overnight. After which time the reaction mixture was filtered and purified by reverse phase HPLC (water/CH3CN, 0.1% TFA 3-70%) to give the title compound (16 mg, 59%).

Workup

  1. filtrationAfter which time the reaction mixture was filtered
  2. custompurified by reverse phase HPLC (water/CH3CN, 0.1% TFA 3-70%)

Sources & evidence

ORD record
ord-bc05a94367904021a3946c69b273a648
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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