1H-1,2,4-Triazole → 7-(cyclohexylmethyl)-5-methyl-N-[4-(methyloxy)phenyl]-imidazo[5,1-f][1,2,4]triazin-2-amine

HRID 2375008Notes

Reaction equation

HRID 2375008 reaction equation
[CH:1]1([CH2:7][C:8]([NH:10][CH:11]([C:13]2[N:18]=[N:17][C:16]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)=[N:15][CH:14]=2)[CH3:12])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=NC=N1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[CH:1]1([CH2:7][C:8]2[N:18]3[C:13]([CH:14]=[N:15][C:16]([NH:19][C:20]4[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=4)=[N:17]3)=[C:11]([CH3:12])[N:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 587119492-cyclohexyl-N-[1-(3-{[4-(methyloxy)phenyl]amino)-1,2,4-triazin-6-yl)ethyl]acetamide2×

Product 1

HCID 114054447-(cyclohexylmethyl)-5-methyl-N-[4-(methyloxy)phenyl]-imidazo[5,1-f][1,2,4]triazin-2-amineYield 71.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Applying the Cyclization Procedure 2, using 2-cyclohexyl-N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]acetamide (Intermediate 69) (100 mg, 0.27 mmol), pyridine (25 mL), 1,2,4 triazole (56 mg, 0.81 mmol) and phosphorus oxychloride (0.040 mL, 0.43 mmol), to afford 7-(cyclohexylmethyl)-5-methyl-N-[4-(methyloxy)phenyl]-imidazo[5,1-f][1,2,4]triazin-2-amine (68 mg) as a yellow solid. MS m/z 352 (M+1).

Sources & evidence

ORD record
ord-c888c872becb4bbf872af56b4bf3d9b3
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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