Benzoyl chloride → N-Cyclopropyl-4-oxazol-5-yl-N-[1-(5-phenyl-[1,2,4]oxadiazol-3-yl)-piperidin-4-yl]-benzamide

HRID 68844Notes

Reaction equation

HRID 68844 reaction equation
[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([C:24](=[NH:27])[NH:25][OH:26])[CH2:20][CH2:19]2)[C:5](=[O:17])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:16][CH:15]=[N:14][CH:13]=3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[C:28](Cl)(=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C>O1CCCC1>[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[N:27]=[C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:26][N:25]=3)[CH2:20][CH2:19]2)[C:5](=[O:17])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[O:16][CH:15]=[N:14][CH:13]=3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 178513431HCID 178513431, compound

Product 1

HCID 68351846N-Cyclopropyl-4-oxazol-5-yl-N-[1-(5-phenyl-[1,2,4]oxadiazol-3-yl)-piperidin-4-yl]-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-cyclopropyl-N-[1-(N-hydroxycarbamimidoyl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide (220 mg), benzoyl chloride (70 μL), and triethylamine (250 μL) in tetrahydrofuran (5 mL) is stirred for 30 min at room temperature before heating to 80° C. for 15 h. The solvent is evaporated and the residue is chromatographed on silica gel (dichloromethane/methanol 93:7) to afford the title compound. LC (method 3): tR=2.09 min; Mass spectrum (ESI+): m/z=456 [M+H]+.

Workup

  1. temperaturebefore heating to 80° C. for 15 h
  2. customThe solvent is evaporated
  3. customthe residue is chromatographed on silica gel (dichloromethane/methanol 93:7)

Sources & evidence

ORD record
ord-f984fe8d093949ab9a4af1d122ab3679
Source dataset
uspto-grants-2014_09
Patent number
US08822471B2

Reaction notes

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