1H-1,2,4-Triazole → HCID 11385366, compound

HRID 2374912Notes

Reaction equation

HRID 2374912 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:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH: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>[CH3:21][C:20]1[N:22]=[C:23]([C:25]2[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=2)[N:16]2[C:17]=1[CH:18]=[N:19][C:14]([NH:13][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=1)=[N:15]2

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 58712006Methyl 4-{[(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)amino]carbonyl}benzoate2×

Product 1

HCID 11385366HCID 11385366, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar manner as described for Example 9, methyl 4-{[(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)amino]carbonyl}benzoate (Intermediate 30) (56 mg, 0.12 mmol), and 1,2,4-triazole (55 mg, 0.80 mmol) in pyridine (2 mL) and phosphorous oxychloride (0.037 mL, 0.40 mmol) gave methyl 4-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}benzoate (11 mg, 20%) as a yellow solid. 1H NMR (CD3OD): δ9.06 (s, 1H), 9.01 (s, 1H), 8.58 (d, J=7.87 Hz, 1H), 8.08 (d, J=7.87 Hz, 1H), 7.62 (t, J=7.87 Hz, 1H), 7.04 (s, 2H), 5.48 (s, 1H), 3.87 (s, 3.75 (s, 3H), 3.71 (s, 6H), 2.59 (s, 3H). MS m/z 449 (M+1).

Sources & evidence

ORD record
ord-aa23ea3e2fa642979e7c937aabfdd97f
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

Loading…