Morpholine → HCID 69067026, compound

HRID 1784099Notes

Reaction equation

HRID 1784099 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]3[O:20][CH2:21][O:22][C:15]=13)=[CH:10][C:9]([O:23][CH3:24])=[C:8]([O:25][CH2:26][C@@H:27]1[O:29][CH2:28]1)[CH:7]=2)#[N:2].[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>C(O)CC>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]3[O:20][CH2:21][O:22][C:15]=13)=[CH:10][C:9]([O:23][CH3:24])=[C:8]([O:25][CH2:26][C@H:27]([OH:29])[CH2:28][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)[CH:7]=2)#[N:2]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86595893HCID 86595893, compound

Product 1

HCID 69067026HCID 69067026, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-cyano-7-[(2R)-2,3-epoxypropoxy]-6-methoxy-4-(2,3-methylenedioxyanilino)quinoline (0.1 g), morpholine (0.11 g) and propanol (5 ml) was stirred and heated to 80° C. for 3 hours. The resultant mixture was evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. The material so obtained was triturated under diethyl ether to give the title compound (0.04 g); NMR Spectrum: (DMSOd6) 2.35-2.52 (m, 6H), 3.56 (m, 4H), 3.93 (s, 3H), 4.04.1 (m, 2H), 4.17 (m, 1H), 4.9 (d, 1H), 5.98 (s, 2), 6.9-6.92 (m, 3H), 7.33 (s, 1H), 7.86 (s, 1H), 8.4 (s, 1H), 9.48 (br s, 1H); Mass Spectrum: M−H− 477.

Workup

  1. customThe resultant mixture was evaporated
  2. customthe residue was purified by column chromatography on silica using
  3. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent
  4. customThe material so obtained
  5. customwas triturated under diethyl ether

Sources & evidence

ORD record
ord-02299f06a64e41adb6ac5ef29d0c9252
Source dataset
uspto-grants-2009_03
Patent number
US07501516B2

Reaction notes

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