Sodium hydride → HCID 24900680, compound

HRID 421652Notes

Reaction equation

HRID 421652 reaction equation
[NH2:1][C:2]1[C:3]([C:15]([NH2:17])=[O:16])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[N:14]=1.[H-].[Na+].[CH3:20][N:21]([CH3:26])[S:22](Cl)(=[O:24])=[O:23]>C1COCC1.CN(C=O)C>[NH2:1][C:2]1[C:3]([C:15]([NH2:17])=[O:16])=[CH:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([S:22]([N:21]([CH3:26])[CH3:20])(=[O:24])=[O:23])[C:6]=2[N:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chlorideHCID 152709842-amino-9H-pyrido[2,3-b]indole-3-carboxamide

Product 1

HCID 24900680HCID 24900680, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of 2-amino-9H-pyrido[2,3-b]indole-3-carboxamide (5, 138 mg, 0.610 mmol) in a 1:1 mixture of THF-DMF (4.5 mL) was added NaH (73.0 mg, 2.50 mmol). The mixture was stirred at RT. After 10-15 min, dimethylsulfamoyl chloride (212 mL, 1.10 mmol) was added and the reaction was stirred for another 2 h. The reaction was quenched with water (50 mL) and poured into a separatory funnel containing EtOAc (100 mL). The mixture was shaken and the layers were separated. The organic layer was washed with brine (50 mL), dried over sodium sulfate, filtered and concentrated. The crude product was purified by HPLC (Phenomenex Luna 15 μm C18, aqueous HCOOH/CH3CN) to give 2-amino-9-[(dimethylamino)sulfonyl]-9H-pyrido[2,3-b]indole-3-carboxamide as a white powder (17, 24.9 mg, 12%). HCOOH standard conditions. DAD Retention time=3.68 min. M+H=334. 1H NMR (300 MHz, DMSO-d6): δ 8.78 (s, 1H), 8.06 (s, 1H), 8.00-7.97 (m, 1H), 7.84-7.81 (m, 1H), 7.72 (br s, 2H), 7.40-7.32 (m, 3H), 3.02 (s, 6H).

Workup

  1. stirringthe reaction was stirred for another 2 h
  2. customThe reaction was quenched with water (50 mL)
  3. additionpoured into a separatory funnel
  4. additioncontaining EtOAc (100 mL)
  5. stirringThe mixture was shaken
  6. customthe layers were separated
  7. washThe organic layer was washed with brine (50 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was purified by HPLC (Phenomenex Luna 15 μm C18, aqueous HCOOH/CH3CN)

Sources & evidence

ORD record
ord-22803941d7ef43fc8d159856a7aa632f
Source dataset
uspto-grants-2012_01
Patent number
US08101604B2

Reaction notes

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