Potassium Hydroxide → HCID 59375485, compound

HRID 2193004Notes

Reaction equation

HRID 2193004 reaction equation
[CH3:1][CH:2]([NH:7][C:8]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]#[C:23][Si](C)(C)C)=[CH:21][C:16]=2[C:15]2[C:14](=[O:28])[NH:13][CH:12]=[CH:11][C:10]=2[N:9]=1)[C:3]([CH3:6])([CH3:5])[CH3:4].[OH-].[K+]>CO.O>[C:22]([C:20]1[CH:19]=[CH:18][C:17]2[C:8]([NH:7][CH:2]([CH3:1])[C:3]([CH3:4])([CH3:6])[CH3:5])=[N:9][C:10]3[CH:11]=[CH:12][NH:13][C:14](=[O:28])[C:15]=3[C:16]=2[CH:21]=1)#[CH:23]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59375513HCID 59375513, compound

Product 1

HCID 59375485HCID 59375485, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 6-[(1,2,2-trimethylpropyl)amino]-9-[(trimethylsilyl)ethynyl]benzo[c]-1,6-naphthyridin-1(2H)-one (20 mg, 0.05 mmol) in MeOH (3.0 mL) was added KOH (6.0 mg, 0.09 mmol). The resulting mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with water (5 mL) and extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with brine (5 mL), dried over magnesium sulfate, filtered, concentrated to afford 9-ethynyl-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one. 1H NMR (300 MHz, CDCl3) δ 10.15 (s, 1H), 7.69 (d, J=8.3 Hz, 1H), 7.62 (d, J=10.1 Hz, 1H), 7.31 (s, 1H), 6.62 (s, 1H), 3.23 (s, 1H), 1.25 (m, 3H), 1.04 (s, 9H). LRMS calculated for C20H21N3O [M+H]+, 320; found 320.

Workup

  1. extractionextracted with ethyl acetate (3×5 mL)
  2. washThe combined organic layers were washed with brine (5 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-aa5912bf877c413d99e7d03f2a676a0f
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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