Potassium Carbonate → HCID 59403439, compound

HRID 1514250Notes

Reaction equation

HRID 1514250 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:28]=[CH:27][C:21]4[CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:20]=4[CH:19]=3)[N:14]=2)[CH:6]=[N:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40]>CN(C)C=O>[Cl:2][C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:28]=[CH:27][C:21]4[CH2:22][CH2:23][N:24]([CH2:36][CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:25][CH2:26][C:20]=4[CH:19]=3)[N:14]=2)[CH:6]=[N:7][C:8]=1[O:9][CH:10]([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 44129294HCID 44129294, compound

Product 1

HCID 59403439HCID 59403439, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

7-(5-{5-Chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride (Example 50) (192 mg, 0.499 mmol) in N,N-dimethylformamide (2 ml) at room temperature was treated with potassium carbonate (103 mg, 0.748 mmol) and ethyl 4-bromobutanoate (0.09 ml, 0.60 mmol). The mixture was heated to 100° C. After ca. 2 hrs, the mixture was cooled and concentrated. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with brine, dried and concentrated to a colourless gum. The crude material was loaded onto a silica gel column and chromatographed, eluting with a gradient of 80-100% ethyl acetate in cyclohexane gave the title compound as a colourless gum, which slowly crystallized on standing (185 mgs).

Workup

  1. temperaturethe mixture was cooled
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe ethyl acetate layer was washed with brine
  5. customdried
  6. concentrationconcentrated to a colourless gum
  7. customchromatographed
  8. washeluting with a gradient of 80-100% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-a0b7e2b60cff4cf7a9696c96a9e67686
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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