Hydrazine → [5-(5-isopropyl-2,4-dimethoxy-phenyl)-4-(1-methyl-1H-indol-5-yl)-4H-[1,2,4]triazol-3-yl]-phenylamine

HRID 76103Notes

Reaction equation

HRID 76103 reaction equation
[CH:1]([C:4]1[C:5]([O:25][CH3:26])=[CH:6][C:7]([O:23][CH3:24])=[C:8]([CH:22]=1)[C:9]([NH:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH3:21])[CH:16]=[CH:15]2)=S)([CH3:3])[CH3:2].[NH2:27][NH2:28].C(N(C(C)C)CC)(C)C.[CH:38]1[CH:43]=[CH:42][C:41]([N:44]=[C:45](Cl)Cl)=[CH:40][CH:39]=1>O1CCOCC1>[CH:1]([C:4]1[C:5]([O:25][CH3:26])=[CH:6][C:7]([O:23][CH3:24])=[C:8]([C:9]2[N:11]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[N:17]([CH3:21])[CH:16]=[CH:15]4)[C:45]([NH:44][C:41]3[CH:42]=[CH:43][CH:38]=[CH:39][CH:40]=3)=[N:27][N:28]=2)[CH:22]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 9321HydrazineHCID 12145Phenylimidocarbonyl chlorideHCID 81531DiisopropylethylamineHCID 59729557HCID 59729557, compound

Product 1

HCID 59729571[5-(5-isopropyl-2,4-dimethoxy-phenyl)-4-(1-methyl-1H-indol-5-yl)-4H-[1,2,4]triazol-3-yl]-phenylamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A flask was charged with 5-isopropyl-2,4-dimethoxy-N-(1-methyl-1H-indol-5-yl)-thiobenzamide (123 mg; 0.33 mmol), dioxane (2 mL), and hydrazine (0.5 mL). The reaction was heated to 100° C. for one hour, and the solvent was removed by evaporation. To the solid cake was added ethyl acetate (10 mL) and 10% aqueous potassium carbonate (1 mL), and it was shaken until the solid was completely dissolved. The organic layer was isolated, and dried with sodium sulfate. To the crude intermediate in the organic layer was added diisopropylethylamine (86 mg, 0.66 mmol) and phenylisocyanide dichloride (88 mg; 1.5 eq.). The reaction was stirred overnight, and washed with saturated aqueous ammonium chloride, dried with sodium sulfate, and the product was purified by column chromatography to give [5-(5-Isopropyl-2,4-dimethoxy-phenyl)-4-(1-methyl-1H-indol-5-yl)-4H-[1,2,4]triazol-3-yl]-phenyl-amine (64 mg).

Workup

  1. customthe solvent was removed by evaporation
  2. additionTo the solid cake was added ethyl acetate (10 mL) and 10% aqueous potassium carbonate (1 mL), and it
  3. dissolutionwas completely dissolved
  4. customThe organic layer was isolated
  5. dry with materialdried with sodium sulfate
  6. stirringThe reaction was stirred overnight
  7. washwashed with saturated aqueous ammonium chloride
  8. dry with materialdried with sodium sulfate
  9. customthe product was purified by column chromatography

Sources & evidence

ORD record
ord-fa7d34f5ad46451b8e1433273d41334d
Source dataset
uspto-grants-2014_09
Patent number
US08835464B2

Reaction notes

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