Morpholine → HCID 59714945, compound

HRID 2223918Notes

Reaction equation

HRID 2223918 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]3([CH2:30][C:31]([OH:33])=O)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:18][CH2:17]2)[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[N:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>ClCCl.CN(C)C=O>[N:40]1([C:31](=[O:33])[CH2:30][C:24]2([CH2:23][CH2:22][N:19]3[CH2:20][CH2:21][CH:16]([N:8]([C:5]4[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=4)[C:9]([C:11]4[O:12][CH:13]=[CH:14][CH:15]=4)=[O:10])[CH2:17][CH2:18]3)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 65578Oxalyl chlorideHCID 59714998HCID 59714998, compound

Product 1

HCID 59714945HCID 59714945, compoundYield 17.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [1-[2-[4-[N-(5-methylpyridin-2-yl)-2-furancarboxamido]piperidin-1-yl]ethyl]cyclohexyl]acetic acid (synthesized in Example 3A-3) (300 mg) in dichloromethane (4 mL) was added N,N-dimethylformamide (1 drop) dropwise and then oxalyl chloride (0.087 mL) under ice cooling. The solution was stirred under ice cooling for 2 hours. A 2 mL aliquot of the reaction solution was taken and it was added to a solution of morpholine (288 mg) in dichloromethane (4 mL) dropwise under ice cooling. The solution was stirred under ice cooling for 1.5 hours. NH silica gel was then added to the reaction solution and it was concentrated under reduced pressure. The residue was purified by chromatography [NH silica gel, hexane-ethyl acetate (1:1)] to give the title compound (60 mg).

Workup

  1. stirringThe solution was stirred under ice cooling for 1.5 hours
  2. additionNH silica gel was then added to the reaction solution and it
  3. concentrationwas concentrated under reduced pressure
  4. customThe residue was purified by chromatography [NH silica gel, hexane-ethyl acetate (1:1)]

Sources & evidence

ORD record
ord-1f1c234f287448be84faef15b7c75daf
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

Loading…