Hydrochloric Acid → HCID 59352748, compound

HRID 2385562Notes

Reaction equation

HRID 2385562 reaction equation
C1(C(=[N:14][C:15]2[N:20]=[C:19]([CH2:21][N:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]4([C:42]5[C:33](=[CH:34][C:35]6[O:40][CH2:39][CH2:38][O:37][C:36]=6[CH:41]=5)[O:32][CH2:31]4)[C:23]3=[O:43])[CH:18]=[CH:17][CH:16]=2)C2C=CC=CC=2)C=CC=CC=1.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[NH2:14][C:15]1[N:20]=[C:19]([CH2:21][N:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]3([C:42]4[C:33](=[CH:34][C:35]5[O:40][CH2:39][CH2:38][O:37][C:36]=5[CH:41]=4)[O:32][CH2:31]3)[C:23]2=[O:43])[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59352111HCID 59352111, compound

Product 1

HCID 59352748HCID 59352748, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1′-({6-[(diphenylmethylidene)amino]pyridin-2-yl}methyl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.18 g, 0.32 mmol) in tetrahydrofuran (10 mL) was added 2 M aqueous hydrochloric acid (0.5 mL). The reaction mixture was stirred at ambient temperature for 10 min, cooled to 0° C. and saturated aqueous sodium bicarbonate (10 mL) was added. The mixture was diluted with ethyl acetate (30 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×25 mL). The combined organic layers was washed with brine (45 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography and eluted with 65% ethyl acetate in hexanes to afford 1′-[(6-aminopyridin-2-yl)methyl]-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.10 g, 76%) as a colorless solid: mp 240-241° C.; 1H NMR (300 MHz, CDCl3) δ7.45-7.35 (m, 1H), 7.25-7.14 (m, 2H), 7.06-6.98 (m, 1H), 6.91-6.86 (m, 1H), 6.59-6.54 (m, 1H), 6.50 (s, 1H), 6.45-6.39 (m, 1H), 6.37 (s, 1H), 5.12-5.03 (m, 1H), 4.99-4.92 (m, 1H), 4.80-4.63 (m, 4H), 4.25-4.05 (m, 4H); 13C NMR (300 MHz, CDCl3) δ 177.5, 157.9, 155.2, 153.0, 144.6, 142.1, 139.0, 138.2, 132.2, 128.8, 123.7, 123.4, 121.2, 111.7, 111.1, 109.6, 107.9, 99.3, 80.0, 64.5, 63.9, 58.1, 45.2; MS (ES+) m/z 401.9 (M+1).

Workup

  1. temperaturecooled to 0° C.
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×25 mL)
  4. washThe combined organic layers was washed with brine (45 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography
  9. washeluted with 65% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6abc88db729a415686b7d9664d662743
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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