Sodium Methoxide → 2-((2-Methoxypyridin-4-yl)methyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

HRID 41569Notes

Reaction equation

HRID 41569 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C:11]3([CH2:19][CH2:18][N:17]([C:20]4[CH:29]=[N:28][C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21]=4)[CH2:16][CH2:15]3)[C:10]2=[O:30])[CH:5]=[CH:4][N:3]=1.[CH3:31][O-:32].[Na+]>CO>[CH3:31][O:32][C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C:11]3([CH2:19][CH2:18][N:17]([C:20]4[CH:29]=[N:28][C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21]=4)[CH2:16][CH2:15]3)[C:10]2=[O:30])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 718111802-((2-Bromopyridin-4-yl)methyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one2×

Product 1

HCID 532596382-((2-Methoxypyridin-4-yl)methyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-oneYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was synthesized from 2-((2-bromopyridin-4-yl)methyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one (prepared according to method D) as follows: A stirred solution of 2-((2-bromopyridin-4-yl)methyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one (synthesized according to method D) (70 mg, 0.15 mmol) and NaOMe (40.6 mg, 0.75 mmol) in MeOH (2 mL) was heated at 100° C. for 18 h. The reaction mixture was cooled to rt and the solvent was evaporated under reduced pressure. Water was added and the mixture was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was washed with hexane to yield the title compound (55 mg, 68%). [1H NMR (300 MHz, CDCl3) ♀ ppm 8.60 (s, 1H), 8.12 (d, 1H), 7.85 (d, 1H), 7.68 (d, 1H), 7.56 (t, 1H), 7.38 (t, 1H), 6.75 (d, 1H), 6.55 (s, 1H), 4.56 (s, 2H), 4.31-4.13 (m, 2H), 3.92 (s, 3H), 3.70-3.55 (m, 2H), 3.25 (br s, 2H), 2.40-2.25 (m, 2H), 1.98-1.80 (m, 4H), 1.78-1.50 (m, 2H); LCMS RtF=1.30 min, [M+H]+=418.0].

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionWater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. washThe crude product was washed with hexane

Sources & evidence

ORD record
ord-ffbe8285b284460d9eb7593ce15b4521
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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