Morpholine → HCID 59295396, compound

HRID 2233293Notes

Reaction equation

HRID 2233293 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2(Br)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:8][C:7]=1[CH2:18]Br)=[O:5])[CH3:2].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C1CCN2C(=NCCC2)CC1>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=2)=[N:8][C:7]=1[CH2:18][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59295387HCID 59295387, compound

Product 1

HCID 59295396HCID 59295396, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

1.25 g 2-(1-Bromo-cyclohexyl)-4-bromomethyl-oxazole-5-carboxylic acid ethyl ester was dissolved in 15 ml tetrahydrofuran. 1.38 ml morpholine and 0.5 ml DBU were added and the reaction mixture stirred at 65° C. for three hours. The solvent was removed in vacuo and the resulting crude material was purified by reversed phase HPLC. The lyophilisate was dissolved in ethyl acetate and washed with saturated NaHCO3 and 2N NaOH solution the organic layer was dried over MgSO4. The solvent was removed in vacuo to obtain 580 mg 2-Cyclohex-1-enyl-4-morpholin-4-ylmethyl-oxazole-5-carboxylic acid ethyl ester as an oil.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting crude material was purified by reversed phase HPLC
  3. dissolutionThe lyophilisate was dissolved in ethyl acetate
  4. washwashed with saturated NaHCO3 and 2N NaOH solution the organic layer
  5. dry with materialwas dried over MgSO4
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-346b232b2d954269bc0986d2bbc495d3
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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