Hydrochloric Acid → HCID 69358771, compound

HRID 1241586Notes

Reaction equation

HRID 1241586 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:6]1[CH2:32][C@@H:7]1[CH2:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]4[O:27][CH2:28][O:29][C:22]=34)=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:30][CH3:31].C(Cl)(Cl)[Cl:34].[ClH:37]>C(Cl)Cl.CO.C(OCC)C.C(O)C>[ClH:34].[ClH:37].[OH:6][C@H:7]([CH2:32][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]4[O:27][CH2:28][O:29][C:22]=34)=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:30][CH3:31]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 31268PyrrolidineHCID 86591150HCID 86591150, compound

Product 1

HCID 69358771HCID 69358771, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of pyrrolidine (0.016 ml), 7-[(2R)-2,3-epoxypropoxy]-6-methoxy-4-(2,3-methylenedioxyanilino)quinazoline (0.03 g), chloroform (0.5 ml) and ethanol (0.5 ml) was stirred and heated to 40° C. for 7 hours. The mixture was evaporated and the residue was dissolved in methylene chloride (4 ml). A polystyrene isocyanate resin (prepared according to J. Amer. Chem. Soc., 1997, 119, 4882; loading: 1 mmol/g; 0.3 g) was added and the mixture was shaken at ambient temperature for 1.5 hours. The resin was removed by filtration and washed with methylene chloride. The filtrate was evaporated and the crude product so obtained was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and a saturated methanolic ammonia solution as eluent. The material so obtained was dissolved in a 9:1 mixture of methylene chloride and methanol (3 ml) and a 2.2M solution. of hydrogen chloride in diethyl ether (1 ml) was added. The precipitate was isolated and dried under vacuum. There was thus obtained the title compound (0.026 g); NMR Spectrum: (DMSOd6 and CF3CO2D) 1.85–2.15 (m, 4H), 3.06–3.25 (m, 2H), 3.31–3.47 (m, 2H), 3.6–3.74 (m, 2H), 4.04 (s, 3H), 4.8 (d,2H), 4.38–4.46 (m, 1H), 6.1 (s, 2H), 6.94–7.05 (m, 3H), 7.49 (s, 1H), 8.27 (s, 1H), 8.88 (s, 1H); Mass Spectrum: M+H+ 439.

Workup

  1. customThe mixture was evaporated
  2. dissolutionthe residue was dissolved in methylene chloride (4 ml)
  3. additionA polystyrene isocyanate resin (prepared according to J. Amer. Chem. Soc., 1997, 119, 4882; loading: 1 mmol/g; 0.3 g) was added
  4. stirringthe mixture was shaken at ambient temperature for 1.5 hours
  5. customThe resin was removed by filtration
  6. washwashed with methylene chloride
  7. customThe filtrate was evaporated
  8. customthe crude product so obtained
  9. customwas purified by column chromatography on silica using
  10. temperatureincreasingly polar mixtures of methylene chloride
  11. customThe material so obtained
  12. customThe precipitate was isolated
  13. customdried under vacuum

Sources & evidence

ORD record
ord-c23617f9856c481fa6682f013875ea90
Source dataset
uspto-grants-2006_10
Patent number
US07115615B2

Reaction notes

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