Thioacetamide → HCID 67357937, compound

HRID 2385551Notes

Reaction equation

HRID 2385551 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[C:7]1([C:27]3[C:18](=[CH:19][C:20]4[O:25][CH2:24][CH2:23][O:22][C:21]=4[CH:26]=3)[O:17][CH2:16]1)[C:8](=[O:15])[N:9]2[CH3:14])=O.[C:28]([NH2:31])(=[S:30])[CH3:29]>O1CCOCC1>[CH3:14][N:9]1[C:10]2[C:6](=[C:5]([C:3]3[N:31]=[C:28]([CH3:29])[S:30][CH:2]=3)[CH:13]=[CH:12][CH:11]=2)[C:7]2([C:27]3[C:18](=[CH:19][C:20]4[O:25][CH2:24][CH2:23][O:22][C:21]=4[CH:26]=3)[O:17][CH2:16]2)[C:8]1=[O:15]

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 86642199HCID 86642199, compound

Product 1

HCID 67357937HCID 67357937, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 4′-(bromoacetyl)-1′-methyl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.25 g, 0.57 mmol) in p-dioxane (15 mL) was added thioacetamide (0.047 g, 0.63 mmol) and the reaction mixture, which became homogeneous upon heating, was heated at 80° C. for 1 h. The reaction mixture was allowed to cool to ambient temperature and was concentrated to dryness in vacuo. The crude product was purified by column chromatography and eluted with a 0% to 100% gradient of ethyl acetate in hexanes to afford 1′-methyl-4′-(2-methyl-1,3-thiazol-4-yl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.076 g, 33%) as an off-white solid: mp 219-220° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ7.42-7.36 (m, 1H), 7.32-7.27 (m, 1H), 6.91 (d, J=7.7 Hz, 1H), 6.54 (s, 1H), 6.36 (s, 1H), 6.22 (s, 1H), 4.81-4.71 (m, 2H), 4.21-4.07 (m, 4H), 3.29 (s, 3H), 2.64 (s, 3H); 13C NMR (75 MHz, CDCl3) δ178.4, 165.2, 156.1, 151.8, 144.4, 137.7, 133.2, 129.2, 128.6, 124.7, 122.2, 116.6, 111.2, 108.2, 99.1, 78.3, 77.4, 64.7, 64.0, 58.8, 27.0, 19.1; MS (ES+) m/z 406.9 (M+1).

Workup

  1. temperatureupon heating
  2. temperatureto cool to ambient temperature
  3. concentrationwas concentrated to dryness in vacuo
  4. customThe crude product was purified by column chromatography
  5. washeluted with a 0% to 100% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-71518837e86a4772aabe361a0caa4aa4
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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