Sodium Hydroxide → HCID 59352668, compound

HRID 1407934Notes

Reaction equation

HRID 1407934 reaction equation
[O:1]=[C:2]1[C:10]2([C:22]3[C:13](=[CH:14][C:15]4[O:20][CH2:19][CH2:18][O:17][C:16]=4[CH:21]=3)[O:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([NH2:29])=[O:28].CO[C:35](OC)([N:37](C)C)[CH3:36].Cl.NO.[OH-].[Na+]>O1CCOCC1.O.C(O)(=O)C>[CH3:36][C:35]1[N:29]=[C:27]([C:26]2[CH:25]=[C:24]([CH:32]=[CH:31][CH:30]=2)[CH2:23][N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:10]3([C:22]4[C:13](=[CH:14][C:15]5[O:20][CH2:19][CH2:18][O:17][C:16]=5[CH:21]=4)[O:12][CH2:11]3)[C:2]2=[O:1])[O:28][N:37]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 443297Hydroxyamine hydrochlorideHCID 59352384HCID 59352384, compound

Product 1

HCID 59352668HCID 59352668, compoundYield 6.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 3-[(2′-oxo-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-1′(2′H)-yl)methyl]benzamide (0.50 g, 1.17 mmol) and N,N-dimethylacetamide dimethyl acetal (0.60 mL, 4.1 mmol) in 1,4-dioxane (10 mL) was stirred at 110° C. for 3 h, allowed to cool to ambient temperature and concentrated in vacuo. Hydroxylamine hydrochloride (0.11 g, 1.6 mmol), 1,4-dioxane (10 mL), glacial acetic acid (10 mL) and 2 M aqueous sodium hydroxide (0.85 mL, 1.70 mmol) were then added and the mixture was heated at 90° C. for 2 h. The mixture was allowed to cool to ambient temperature and water was added, causing a precipitate to be deposited. The solid was collected by filtration, washed with water and hexanes and recrystallized from dichloromethane/hexanes to afford 1′-[3-(3-methyl-1,2,4-oxadiazol-5-yl)benzyl]-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.038 g, 6%) as a colorless solid: mp 80-89° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.09-8.12 (m, 2H), 7.54-7.57 (m, 2H), 7.15-7.18 (m, 2H), 7.00-7.03 (m, 1H), 6.74-6.77 (m, 1H), 6.50 (s, 1H), 6.29 (s, 1H), 5.14-5.17 (m, 1H), 4.89-4.92 (m, 2H), 4.65-4.67 (m, 1H), 4.13-4.17 (m, 4H), 2.43 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 177.6, 174.9, 167.9, 155.3, 144.7, 141.7, 138.4, 137.0, 132.3, 131.4, 129.9, 128.9, 127.4, 126.8, 124.8, 124.1, 123.7, 120.8, 111.6, 109.1, 99.5, 80.2, 64.5, 63.9, 58.1, 43.7, 11.7; MS (ES+) m/z 467.8 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. temperaturethe mixture was heated at 90° C. for 2 h
  3. temperatureto cool to ambient temperature
  4. filtrationThe solid was collected by filtration
  5. washwashed with water and hexanes
  6. customrecrystallized from dichloromethane/hexanes

Sources & evidence

ORD record
ord-69c1d6fc76f74afb91f27284bda1e8ca
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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