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Dimethylamine → 3-(1-{[2-(dimethylamino)ethyl]sulfonyl}-4-piperidinyl)-5-phenyl-1H-indole-7-carboxamide

HRID 2267510
Notes
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Reaction equation

HRID 2267510 reaction equation
Cl[CH2:2][CH2:3][S:4]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[C:21]3[C:16](=[C:17]([C:28]([NH2:30])=[O:29])[CH:18]=[C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:8]1)(=[O:6])=[O:5].[CH3:31][NH:32][CH3:33].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC#N>[CH3:31][N:32]([CH3:33])[CH2:2][CH2:3][S:4]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[C:21]3[C:16](=[C:17]([C:28]([NH2:30])=[O:29])[CH:18]=[C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:8]1)(=[O:6])=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 674DimethylamineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 590033063-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide

Product 1

HCID 114962033-(1-{[2-(dimethylamino)ethyl]sulfonyl}-4-piperidinyl)-5-phenyl-1H-indole-7-carboxamideYield 48.9%

Reagents, catalysts & solvents

1
HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide (26 mg, 0.063 mmol) in CH3CN (5 mL), dimethylamine (0.16 mL, 0.315 mmol), K2CO3 (35 mg, 0.252 mmol) and NaI (cat. 0.5 mg) were added. The reaction mixture was stirred at 80° C. for 16 hours. The solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulfate, filtered and the solvent removed under reduced pressure. The resulting residue was purified by reverse phase HPLC (CH3CN/water, 0.1% TFA) to give title compound (14 mg, 48%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe resulting residue was purified by reverse phase HPLC (CH3CN/water, 0.1% TFA)

Sources & evidence

ORD record
ord-75ff698322674d04811461320869195c
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07858796B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes