Morpholine → HCID 69218736, compound

HRID 272736Notes

Reaction equation

HRID 272736 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[NH:17][C:16]3[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:15]=3[C:14](=[O:23])[NH:13][C:12]=2[CH:24]=1)(=O)=O.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>CN(C=O)C.C(OCC)(=O)C>[Cl:22][C:19]1[CH:20]=[CH:21][C:15]2[C:14](=[O:23])[NH:13][C:12]3[CH:24]=[C:8]([CH2:7][CH2:6][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[CH:9]=[CH:10][C:11]=3[NH:17][C:16]=2[CH:18]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 87737484HCID 87737484, compound

Product 1

HCID 69218736HCID 69218736, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of Example 641A (360 mg, 0.98 mmol) in DMF (5 mL) was treated with morpholine (200 μL) and heated at 50° C. for 24 hours. The mixture was then cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered and concentrated. The concentrate was purified by column chromatography on silica gel to provide the title compound. MS (ESI) m/e 358 (M+H)+; 1H NMR (300 MHz, DMSO-d.6 □ 9.84 (s, 1H), 7.97 (s, 1H), 7.67 (d, J=8.5 Hz, 1H), 7.05 (d, J=2.0 Hz, 1H), 6.91 (dd, J=8.5, 2.0 Hz, 1H), 6.81-6.89 (m, 3H), 3.55-3.58 (m, 4H), 2.57-2.62 (m, 2H), 2.37-2.45 (m, 6H).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1a613412ba024f9baa01c25c89f0b444
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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