Diisopropylethylamine → N-Cyclopropyl-N-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-4-(4-methyl-oxazol-5-yl)-benzamide

HRID 68840Notes

Reaction equation

HRID 68840 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1.[CH:16]1([NH:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]3[O:30][N:29]=[C:28]([CH:31]([CH3:33])[CH3:32])[N:27]=3)[CH2:22][CH2:21]2)[CH2:18][CH2:17]1.C(N(C(C)C)C(C)C)C>ClCCl>[CH:16]1([N:19]([CH:20]2[CH2:25][CH2:24][N:23]([C:26]3[O:30][N:29]=[C:28]([CH:31]([CH3:33])[CH3:32])[N:27]=3)[CH2:22][CH2:21]2)[C:11](=[O:12])[C:10]2[CH:14]=[CH:15][C:7]([C:6]3[O:5][CH:4]=[N:3][C:2]=3[CH3:1])=[CH:8][CH:9]=2)[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 68290028N-cyclopropyl-1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-amineHCID 866782114-(4-Methyl-oxazol-5-yl)-benzoyl chloride

Product 1

HCID 68351856N-Cyclopropyl-N-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-4-(4-methyl-oxazol-5-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Methyl-oxazol-5-yl)-benzoyl chloride (89 mg) is added portionwise to a mixture of cyclopropyl-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-amine (100 mg) and ethyldiisopropylamine (100 μL) in dichloromethane (5 mL). The mixture is stirred for 1 h at room temperature, washed with water and 1 M HCl, dried over Na2SO4 and concentrated in vacuo. The residue is triturated with diethyl ether to give the title compound. LC (method 6): tR=1.83 min; Mass spectrum (ESI+): m/z=436 [M+H]+.

Workup

  1. washwashed with water and 1 M HCl
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue is triturated with diethyl ether

Sources & evidence

ORD record
ord-8819a428f9dd404b83f06f5f6ccdd2c9
Source dataset
uspto-grants-2014_09
Patent number
US08822471B2

Reaction notes

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