4-Methylmorpholine → 2-[1-[(2,5-dimethylphenyl)acetyl]-4-piperidinyl]-N-methyl-N-[(1R)-1-phenylpropyl]-4-oxazolecarboxamide

HRID 2043735Notes

Reaction equation

HRID 2043735 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[O:19][CH:20]=[C:21]([C:23](O)=[O:24])[N:22]=2)[CH2:14][CH2:13]1)=[O:11].Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.CC1C=CC(C)=CC=1CC(N1CCC(C2SC=C([C:67]([N:69](C)[C@@H:70]([C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=3)[CH2:71][CH3:72])=O)N=2)CC1)=O>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][C:10]([N:12]1[CH2:13][CH2:14][CH:15]([C:18]2[O:19][CH:20]=[C:21]([C:23]([N:69]([CH3:67])[C@@H:70]([C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=3)[CH2:71][CH3:72])=[O:24])[N:22]=2)[CH2:16][CH2:17]1)=[O:11]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 674615172-[1-[(2,5-dimethylphenyl)acetyl]-4-piperidinyl]-N-methyl-N-[(1R)-1-phenylpropyl]-4-thiazolecarboxamideHCID 674616912-[1-[(2,5-Dimethylphenyl)acetyl]-4-piperidinyl]-4-oxazolecarboxylic acid2×

Product 1

HCID 674628362-[1-[(2,5-dimethylphenyl)acetyl]-4-piperidinyl]-N-methyl-N-[(1R)-1-phenylpropyl]-4-oxazolecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-[1-[(2,5-dimethylphenyl)acetyl]-4-piperidinyl]-4-oxazolecarboxylic acid (i.e. the product of Example 9, Step F) (245 mg, 0.72 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (153 mg, 80 mmol) and 4-methylmorpholine (88 μL) in 3 mL of dichloromethane were stirred at room temperature for 15 minutes. (α,R)-α-Ethyl-N-methylbenzenemethanamine (i.e. the product of Example 1, Step C) (0.80 mmol, 119 mg) was added and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with dichloromethane, washed with 1 N aqueous hydrochloric acid and water, dried over MgSO4 and concentrated under reduced pressure. The products were purified by silica gel chromatography using 50-100% ethyl acetate in hexanes as eluant to give 90 mg of the title product, a compound of the present invention as an oil.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature overnight
  2. washwashed with 1 N aqueous hydrochloric acid and water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe products were purified by silica gel chromatography

Sources & evidence

ORD record
ord-5e91b24f3ea44d56b1091c9f20747f3c
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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