Morpholine → CVT-10216

HRID 1694650Notes

Reaction equation

HRID 1694650 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][C:17]([O:23][CH2:24][C:25]4[CH:26]=[C:27]([CH:34]=[CH:35][CH:36]=4)[C:28]([O:30]CC=C)=[O:29])=[CH:18][CH:19]=3)[O:14][CH:13]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].N1CCOCC1>O1CCCC1>[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][C:17]([O:23][CH2:24][C:25]4[CH:26]=[C:27]([CH:34]=[CH:35][CH:36]=4)[C:28]([OH:30])=[O:29])=[CH:18][CH:19]=3)[O:14][CH:13]=2)=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 24961712HCID 24961712, compound

Product 1

HCID 23661666CVT-10216

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of prop-2-enyl 3-[(3-{4-[(methylsulfonyl)amino]phenyl}-4-oxochromen-7-yloxy)methyl]benzoate (88.8 mg, 0.176 mmol), tetrakis(triphenyl-phosphine)palladium(0) (10 mg, 0.009 mmol) in dry tetrahydrofuran 2 ml) was added morpholine (77 mg, 0.88 mmol), and the mixture was stirred at room temperature under argon for 2 hours. Solvent was then removed reduced pressure, and the residue dissolved in acetone, mixed with silica gel, the solvent removed under reduced pressure, and the silica gel eluted with methylene chloride/methanol (95/5) containing 1% acetic acid, to provide 3-[(3-{4-[(methylsulfonyl)amino]phenyl}-4-oxochromen-7-yloxy)methyl]benzoic acid; 1H NMR (400 MHz, DMSO-d6) δ: 13.1 (br s, 1H), 9.84 (s, 1H), 8.47 (s, 1H), 8.08-8.06 (m, 2H), 7.94 (d, 1H, J=7.8 Hz), 7.76 (d, 1H, J=7.7 Hz), 7.58-7.45 (m, 3H), 7.30 (d, 1H, J=1.8 Hz), 7.27 (d, 2H, J=8.5 Hz), 7.20 (dd, 1H, J=1.8 Hz, J=8.9 Hz), 5.38 (s, 2H), 3.03 (s, 3H). (ESI) m/z 466 (M+H)+.

Workup

  1. customSolvent was then removed reduced pressure
  2. dissolutionthe residue dissolved in acetone
  3. additionmixed with silica gel
  4. customthe solvent removed under reduced pressure
  5. washthe silica gel eluted with methylene chloride/methanol (95/5)
  6. additioncontaining 1% acetic acid

Sources & evidence

ORD record
ord-7ffa4d32021f4d54851a55d10940bfe2
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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