Thiourea → HCID 86674039, compound

HRID 1965802Notes

Reaction equation

HRID 1965802 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.[NH2:28][C:29]([NH2:31])=[S:30]>C(O)C>[NH2:31][C:29]1[S:30][CH:2]=[C:3]([C:5]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:6]=2[C:7]2([C:27]4[C:18](=[CH:19][C:20]5[O:25][CH2:24][CH2:23][O:22][C:21]=5[CH:26]=4)[O:17][CH2:16]2)[C:8](=[O:15])[N:9]3[CH3:14])[N:28]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86642199HCID 86642199, compound

Product 1

HCID 86674039HCID 86674039, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4′-(bromoacetyl)-1′-methyl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.20 g, 0.47 mmol) in anhydrous ethanol (10 mL) was added thiourea (0.039 g, 0.51 mmol) and the reaction mixture was heated at reflux 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 10% gradient of methanol in dichloromethane to afford 4′-(2-amino-1,3-thiazol-4-yl)-1′-methyl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one (0.159 g, 84%) as a pale yellow solid: mp 233-234° C. (dec.) (dichloromethane/methanol); 1H NMR (300 MHz, CDCl3) δ7.44-7.37 (m, 1H), 7.23 (d, J=7.9 Hz, 1H), 6.95 (d, J=7.9 Hz, 1H), 6.57-6.42 (br m, 2H), 6.37 (s, 1H), 6.22 (s, 1H), 5.80 (s, 1H), 4.80-4.73 (m, 2H), 4.22-4.07 (m, 4H), 3.28 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 178.0, 168.2, 155.7, 144.8, 144.4, 138.1, 129.7, 129.4, 124.3, 121.9, 111.4, 109.4, 105.9, 99.2, 78.4, 77.4, 64.7, 64.0, 58.6, 27.1; MS (ES+) m/z 408.3 (M+1).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. concentrationwas concentrated to dryness in vacuo
  4. customThe crude product was purified by column chromatography
  5. washeluted with a 0% to 10% gradient of methanol in dichloromethane

Sources & evidence

ORD record
ord-6c984d7b092f4c918b68b27edfa8693a
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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