Morpholine → 1-Methyl-5-{3-[4-(morpholine-4-carbonyl)-phenyl]-3-o-tolyl-propionyl}-1H-pyridin-2-one

HRID 1617705Notes

Reaction equation

HRID 1617705 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]([C:9](=[O:28])[CH2:10][CH:11]([C:19]2[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][CH:20]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[CH:3]1.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>O1CCCC1>[CH3:1][N:2]1[CH:3]=[C:4]([C:9](=[O:28])[CH2:10][CH:11]([C:19]2[CH:27]=[CH:26][C:22]([C:23]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[O:25])=[CH:21][CH:20]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH:5]=[CH:6][C:7]1=[O:8]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 670155254-[3-(1-Methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-benzoic acid

Product 1

HCID 666685521-Methyl-5-{3-[4-(morpholine-4-carbonyl)-phenyl]-3-o-tolyl-propionyl}-1H-pyridin-2-oneYield 105.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture 4-[3-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3-oxo-1-o-tolyl-propyl]-benzoic acid (60 mg), morpholine (17 mg), benzotriazol-1-yloxytris(dimethylamino) phosphonium hexafluorophosphate (108 mg, BOP reagent) and N-ethyldiisopropylamine (62 mg) in tetrahydrofuran (0.6 ml) was stirred overnight at room temperature. The mixture was concentrated to dryness. The product was purified by chromatography (SiO2, dichloromethane/methanol 1:0 to 9:1) to give the title compound (75 mg) as a colorless foam, MS (ESI+): m/z=445.4 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customThe product was purified by chromatography (SiO2, dichloromethane/methanol 1:0 to 9:1)

Sources & evidence

ORD record
ord-135ce512a30144ca95e4b38725978190
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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