Ethanol → HCID 66758355, compound

HRID 1983632Notes

Reaction equation

HRID 1983632 reaction equation
C([C:4]1[C:9]2[CH2:10][C:11](=[CH:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][C:25]([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)([OH:28])[CH2:24][CH2:23]3)[C:12]3[C:13]([O:18][C:8]=2[CH:7]=[CH:6][CH:5]=1)=[N:14][CH:15]=[CH:16][CH:17]=3)(O)=O.C1C=CC(OP([O:48][C:49]2[CH:54]=CC=CC=2)(N=[N+]=[N-])=O)=CC=1.C([N:57]([CH2:60]C)CC)C.C([OH:64])C>C(OCC)(=O)C>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([C:25]2([OH:28])[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][CH:19]=[C:11]3[C:12]4[C:13](=[N:14][CH:15]=[CH:16][CH:17]=4)[O:18][C:8]4[CH:7]=[CH:6][CH:5]=[C:4]([NH:57][C:60]([O:48][CH2:49][CH3:54])=[O:64])[C:9]=4[CH2:10]3)[CH2:23][CH2:24]2)=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 667586701-[3-(7-Carboxy-5,11-dihydro[1]benzoxepino[2,3-b]pyridin-5-ylidene)propyl]-4-(4-chlorophenyl)piperidin-4-ol

Product 1

HCID 66758355HCID 66758355, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of product of example 118 (490 mg) and diphenylphosphonic azide (0.28 ml) was stirred at 110° C. for 30minutes. After the mixture was cooled, and triethylamine (0.14 ml) and ethanol (5 ml) were added, and the mixture was heated to reflux for 8 hours. The reaction mixture was diluted with ethyl acetate and filtered through Celite. The filtrate was washed with saturated aqueous sodium bicarbonate, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (chloroform: methanol=10:1) to give the titled compound (210 mg).

Workup

  1. temperatureAfter the mixture was cooled
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 8 hours
  4. filtrationfiltered through Celite
  5. washThe filtrate was washed with saturated aqueous sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (chloroform: methanol=10:1)

Sources & evidence

ORD record
ord-477628309f264d9f8ddb79022f573dcf
Source dataset
uspto-grants-2009_06
Patent number
US07541365B2

Reaction notes

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