1H-1,2,4-Triazole → 7-(3-furyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine

HRID 2374926Notes

Reaction equation

HRID 2374926 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[N:15]=[N:16][C:17]([CH:20]([NH:22][C:23]([C:25]3[CH:29]=[CH:28][O:27][CH:26]=3)=O)[CH3:21])=[CH:18][N:19]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].N1C=NC=N1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[O:27]1[CH:28]=[CH:29][C:25]([C:23]2[N:16]3[C:17]([CH:18]=[N:19][C:14]([NH:13][C:5]4[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=4)=[N:15]3)=[C:20]([CH3:21])[N:22]=2)=[CH:26]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 58711927N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)-3-furamide2×

Product 1

HCID 112227507-(3-furyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amineYield 51%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar manner as described for Example 9, N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)-3-furamide (Intermediate 37) (211 mg, 0.53 mmol), and 1,2,4-triazole (220 mg, 3.18 mmol) in pyridine (4 mL) and phosphorous oxychloride (0.15 mL, 1.60 mmol) gave 7-(3-furyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (102 mg, 51%) as a yellow solid. 1H NMR (CDCl3): δ8.78 (s, 1H), 8.56 (s, 1H), 7.52 (t, J=1.65 Hz, 1H), 7.20 (d, J=1.65, 1H), 6.87 (s, 2H), 6.82 (s, 1H), 3.90 (s, 6H), 3.87 (s, 3H), 2.60 (s, 3H). MS m/z 381 (M+1).

Sources & evidence

ORD record
ord-3062ff4e681143b28bf270e847a923df
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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