Diisopropylethylamine → N-(1-Cyano-piperidin-4-yl)-N-cyclopropyl-4-oxazol-5-yl-benzamide

HRID 68755Notes

Reaction equation

HRID 68755 reaction equation
[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][NH:21][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.[CH2:24]([N:26](C(C)C)C(C)C)C>ClCCl.O1CCCC1>[C:24]([N:21]1[CH2:22][CH2:23][CH:18]([N:4]([CH:1]2[CH2:3][CH2:2]2)[C:5](=[O:17])[C:6]2[CH:7]=[CH:8][C:9]([C:12]3[O:16][CH:15]=[N:14][CH:13]=3)=[CH:10][CH:11]=2)[CH2:19][CH2:20]1)#[N:26]

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 68289931N-Cyclopropyl-4-oxazol-5-yl-N-piperidin-4-yl-benzamide

Product 1

HCID 86678209N-(1-Cyano-piperidin-4-yl)-N-cyclopropyl-4-oxazol-5-yl-benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Bromonitirile (1.96 g) is added to a solution of N-cyclopropyl-4-oxazol-5-yl-N-piperidin-4-yl-benzamide (3.50 g) and ethyldiisopropylamine (9.60 mL) in dichloromethane (125 mL) and tetrahydrofuran (125 mL) and the reaction mixture is stirred over night at room temperature. The reaction mixture is washed with water and the organic phase is dried over Na2SO4 and concentrated in vacuo. The residue is triturated with diethyl ether to afford the title compound. LC (method 3): tR=1.55 min; Mass spectrum (ESI+): m/z=337 [M+H]+.

Workup

  1. washThe reaction mixture is washed with water
  2. dry with materialthe organic phase is dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue is triturated with diethyl ether

Sources & evidence

ORD record
ord-56e572bcba22477aaf0a8fbb7961a718
Source dataset
uspto-grants-2014_09
Patent number
US08822471B2

Reaction notes

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