Morpholine → HCID 86609836, compound

HRID 2116839Notes

Reaction equation

HRID 2116839 reaction equation
[C:1]([CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[N:28][OH:29])[CH2:14][O:15][C:16]2[CH:27]=[CH:26][C:19]([C:20]([O:22]CC=C)=[O:21])=[CH:18][CH:17]=2)=[CH:9][C:8]=1[C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:3])[CH3:2].N1CCOCC1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[N:28][OH:29])[CH2:14][O:15][C:16]2[CH:27]=[CH:26][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)=[CH:9][C:8]=1[C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 86609837HCID 86609837, compound

Product 1

HCID 86609836HCID 86609836, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

360 mg (0.8 mmol) of allyl 4-{2-[4-(acetylethylamino)-3-tert-butylphenyl]-2-hydroxyiminoethoxy}benzoate are dissolved in 10 ml of THF. 48 mg (0.04 mmol) of tetrakis(triphenylphosphine)palladium are added and the medium is stirred for 5 min. 73 μl (0.8 mmol) of morpholine are then added and the reaction medium is stirred for 15 hours. After treatment with 1N hydrochloric acid solution and extraction with ethyl acetate, the residue is purified by chromatography (eluent: 5/5 heptane/ethyl acetate). A white powder is obtained (m.p.=192° C., m=200 mg, yield=60%); (1H NMR (DMSO): 1.05-1.07 (t, 3H); 1.29 (s, 9H); 1.64 (s, 3H); 2.73 (m, 1H); 4.13 (m, 1H); 5.33 (s, 2H); 6.46 (1H); 6.6 (1H); 7.07-7.09 (d, J=8.1 Hz, 1H); 7.51-7.53 (d, J=8 Hz, 1H); 7.54-7.64 (m, 2H); 7.86 (s, 1H); 12.1 (s, 1H)).

Workup

  1. stirringthe reaction medium is stirred for 15 hours
  2. extractionAfter treatment with 1N hydrochloric acid solution and extraction with ethyl acetate
  3. customthe residue is purified by chromatography (eluent: 5/5 heptane/ethyl acetate)
  4. customA white powder is obtained (m.p.=192° C., m=200 mg, yield=60%)

Sources & evidence

ORD record
ord-eb6242d717ed4fdfaf4dcc2fa2f61211
Source dataset
uspto-grants-2008_10
Patent number
US07439396B2

Reaction notes

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