Trifluoroacetic anhydride → HCID 59352558, compound

HRID 1407940Notes

Reaction equation

HRID 1407940 reaction equation
O[N:2]=[CH:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]3([C:32]4[C:23](=[CH:24][C:25]5[O:30][CH2:29][CH2:28][O:27][C:26]=5[CH:31]=4)[O:22][CH2:21]3)[C:13]2=[O:33])=[CH:7][N:6]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCCC1.C(=O)(O)[O-].[Na+]>[N:4]1[CH:3]=[N:2][N:6]2[CH:7]=[C:8]([CH2:11][N:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]4([C:32]5[C:23](=[CH:24][C:25]6[O:30][CH2:29][CH2:28][O:27][C:26]=6[CH:31]=5)[O:22][CH2:21]4)[C:13]3=[O:33])[CH:9]=[CH:10][C:5]=12

Participants

5

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 178517519HCID 178517519, compound

Product 1

HCID 59352558HCID 59352558, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a cooled (0° C.) suspension of N′-hydroxy-N-{5-[(2′-oxo-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-1′(2′H)-yl)methyl]pyridin-2-yl}imidoformamide (0.22 g, 0.5 mmol) in tetrahydrofuran (7 mL) was slowly added trifluoroacetic anhydride (0.08 mL, 0.54 mmol). The mixture was stirred at ambient temperature for 3 h, diluted with saturated aqueous sodium bicarbonate (10 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers was washed with saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography and eluted with a 50% to 65% gradient of ethyl acetate in hexanes to afford 1′-([1,2,4]triazolo[1,5-a]pyridin-6-ylmethyl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.11 g, 54%) as a colorless solid: mp 207-209° C.; 1H NMR (300 MHz, DMSO-d6) δ8.65 (s, 1H), 8.37 (s, 1H), 7.82-7.77 (m, 1H), 7.61-7.55 (m, 1H), 7.30-7.17 (m, 2H), 7.11-7.04 (m, 1H), 6.90-6.85 (m, 1H), 6.52 (s, 1H), 6.18 (s, 1H), 5.03 (ABq, J=40.9, 15.6 Hz, 2H), 4.80 (ABq, J=79.6, 9.0 Hz, 2H), 4.23-4.09 (m, 4H); 13C NMR (75 MHz, DMSO-d6) δ 177.7, 155.2, 154.2, 149.9, 144.8, 141.2, 138.4, 132.1, 129.8, 129.0, 127.0, 124.4, 124.0, 123.0, 120.5, 117.4, 111.4, 108.6, 99.5, 80.0, 64.5, 63.9, 58.0, 41.2; MS (ES+) m/z 426.9 (M+1).

Workup

  1. temperatureTo a cooled
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers was washed with saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluted with a 50% to 65% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-98c3fc6cae6d4925a221d220f4572887
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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