Triethylamine → HCID 15346977, compound

HRID 583126Notes

Reaction equation

HRID 583126 reaction equation
C(N(CC)CC)C.[CH:8]1([CH2:14]Br)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[NH2:16][C:17]1[C:22]([Cl:23])=[CH:21][C:20]([C:24]2[O:28][C:27](=[O:29])[N:26]([CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[N:25]=2)=[C:19]([O:36][CH3:37])[CH:18]=1>C(#N)C>[NH2:16][C:17]1[C:22]([Cl:23])=[CH:21][C:20]([C:24]2[O:28][C:27](=[O:29])[N:26]([CH:30]3[CH2:31][CH2:32][N:33]([CH2:14][CH:8]4[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]4)[CH2:34][CH2:35]3)[N:25]=2)=[C:19]([O:36][CH3:37])[CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 137636Cyclohexane, (bromomethyl)-HCID 9801427HCID 9801427, compound

Product 1

HCID 15346977HCID 15346977, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
70 °C

Procedure

2.01 ml (13.92 mmol) of triethylamine and then 0.92 g (5.2 mmol) of cyclohexylmethyl bromide in 5 ml of acetonitrile are successively added at room temperature, under an argon atmosphere and with magnetic stirring, to a solution of 1.13 g (3.48 mmol) of 5-(4-amino-5-chloro-2-methoxyphenyl)-3-(piperidin-4-yl)-1,3,4-oxadiazol-2(3H)-one in 40 ml of acetonitrile and the mixture is stirred at 70° C. for 2 days. The solvent is evaporated under reduced pressure, the residue is taken up in chloroform, the solution is washed a number of times with water and dried, the solvent is evaporated under reduced pressure and the residue is crystallized from acetone. 0.7 g of white solid is obtained. Melting point: 186.5-186.7° C.

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. washthe solution is washed a number of times with water
  3. customdried
  4. customthe solvent is evaporated under reduced pressure
  5. customthe residue is crystallized from acetone

Sources & evidence

ORD record
ord-45012630e396437bad76040ea0015119
Source dataset
uspto-grants-1999_07
Patent number
US05929089

Reaction notes

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