1H-1,2,4-Triazole → HCID 178457847, compound

HRID 518744Notes

Reaction equation

HRID 518744 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.Cl[C:9]1[CH:10]=[CH:11][C:12]([N+:28]([O-:30])=[O:29])=[C:13]([NH:15][C@@H:16]2[CH2:21][CH2:20][C@H:19]([C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH:14]=1>CN1C(=O)CCC1>[CH:25]([NH:24][C:22]([C@H:19]1[CH2:18][CH2:17][C@@H:16]([NH:15][C:13]2[CH:14]=[C:9]([N:3]3[CH:7]=[N:6][CH:5]=[N:4]3)[CH:10]=[CH:11][C:12]=2[N+:28]([O-:30])=[O:29])[CH2:21][CH2:20]1)=[O:23])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 178457829HCID 178457829, compound

Product 1

HCID 178457847HCID 178457847, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a suspension of sodium hydride (70.6 mg, 2.94 mmol) and 1H-1,2,4-triazole (203 mg, 2.94 mmol) in NMP (1 mL) was added cis-4-(5-chloro-2-nitrophenylamino)-N-isopropylcyclohexanecarboxamide (100 mg, 0.294 mmol). The resulting suspension was irradiated in a microwave reactor for 1 hour at 150° C. The reaction mixture was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc (×2). The combined organic layers were then washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to provide a yellow oil that crystallized upon standing to provide cis-N-isopropyl-4-(2-nitro-5-(1H-1,2,4-triazol-1-yl)phenylamino)cyclohexanecarboxamide as a yellow solid (100 mg, 91% yield).

Workup

  1. customThe resulting suspension was irradiated in a microwave reactor for 1 hour at 150° C
  2. customThe reaction mixture was partitioned between water and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc (×2)
  4. washThe combined organic layers were then washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto provide a yellow oil that
  9. customcrystallized

Sources & evidence

ORD record
ord-0fe7fbfd43464d4387d40f62ea9a1aa8
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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