1H-1,2,4-Triazole → HCID 11785499, compound

HRID 133480Notes

Reaction equation

HRID 133480 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C@@H:7]([C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=2)[C:27]#[N:28])[C@@H:8]([NH:10][CH:11]([C:17]2[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=2)[C:12]([C:15]#[N:16])([CH3:14])[CH3:13])[CH3:9])=[CH:4][CH:3]=1.[NH:34]1[CH:38]=[N:37][CH:36]=[N:35]1.C([O-])([O-])=O.[K+].[K+]>CN1CCCC1=O.CCOCC.[Cu]I>[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C@@H:7]([C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=2)[C:27]#[N:28])[C@@H:8]([NH:10][CH:11]([C:17]2[CH:22]=[CH:21][C:20]([N:34]3[CH:38]=[N:37][CH:36]=[N:35]3)=[CH:19][CH:18]=2)[C:12]([C:15]#[N:16])([CH3:14])[CH3:13])[CH3:9])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 11785717HCID 11785717, compound

Product 1

HCID 11785499HCID 11785499, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
195 °C

Procedure

To a solution of 22.5 mg (0.043 mmol) of 3-(1(S)-(4-chlorobenzyl)-2(S)-((1-(4-bromophenyl)-2-cyano-2-methylpropyl)amino)propyl)benzonitrile in 0.5 mL of N-methyl-pyrrolidone, 12 mg (0.173 mmol) of 1,2,4-triazole, 2.3 mg of CuI and 24 mg of K2CO3 were added. The mixture was heated in a microwave reactor at 195° C. for 4 hr. The reaction was diluted with ether, washed with water, brine, dried and concentrated. The residue was purified by prep TLC using 50% EtOAc-hexane to isolate the title compound.

Workup

  1. washwashed with water, brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by prep TLC

Sources & evidence

ORD record
ord-08a0ee66a0154e12ad6b0e63f9a9221c
Source dataset
uspto-grants-2008_06
Patent number
US07390835B2

Reaction notes

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