Sodium Hydroxide → 1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-6-carboxamide

HRID 1618533Notes

Reaction equation

HRID 1618533 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:19]3[C:27]4[C:22](=[N:23][CH:24]=[C:25]([C:28]#[N:29])[CH:26]=4)[C:21]([CH3:31])([CH3:30])[CH2:20]3)=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1.[OH-:32].[Na+]>CCO.O>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:19]3[C:27]4[C:22](=[N:23][CH:24]=[C:25]([C:28]([NH2:29])=[O:32])[CH:26]=4)[C:21]([CH3:31])([CH3:30])[CH2:20]3)=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 672852091-(7-Fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile

Product 1

HCID 509389481-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-6-carboxamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-(7-Fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile (80 mg, 0.195 mmol) in EtOH (3 mL) was treated with sodium hydroxide (156 mg, 3.91 mmol) in water (1.0 mL). The reaction was heated at reflux for 3 h. After this time the reaction was evaporated in vacuo. Reverse phase HPLC (10% to 60% acetonitrile in water) gave 1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-6-carboxamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.72 (1H, ddd, J=4.8, 1.8, 1.1 Hz), 8.34 (1H, d, J=1.8 Hz), 7.99-8.06 (1H, m), 7.80-7.96 (4H, m), 7.48-7.61 (2H, m), 7.31 (1H, br. s.), 6.61 (1H, d, J=1.8 Hz), 3.90-3.99 (1H, m), 3.85 (1H, d, J=9.4 Hz), 2.27 (3H, s), 1.53 (3H, s), 1.45 (3H, s). Mass Spectrum (ESI) m/e=428 (M+1).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 3 h
  3. customAfter this time the reaction was evaporated in vacuo

Sources & evidence

ORD record
ord-3a2ab997dc134528b48354eaaa70d121
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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