1H-1,2,4-Triazole → HCID 11200247, compound

HRID 2374922Notes

Reaction equation

HRID 2374922 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([NH:9][CH:10]([C:12]1[N:17]=[N:16][C:15]([NH:18][C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=2)=[N:14][CH:13]=1)[CH3:11])=O.N1C=NC=N1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[CH3:11][C:10]1[N:9]=[C:7]([C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=2)[N:17]2[C:12]=1[CH:13]=[N:14][C:15]([NH:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=1)=[N:16]2

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 58711996HCID 58711996, compound2×

Product 1

HCID 11200247HCID 11200247, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar manner as described for Example 9, 1-methyl-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)-1H-pyrrole-2-carboxamide (Intermediate 35) (222 mg, 0.54 mmol), and 1,2,4-triazole (220 mg, 3.2 mmol) in pyridine (10 mL) and phosphorous oxychloride (0.15 mL, 1.6 mmol) gave 5-methyl-7-(1-methyl-1H-pyrrol-2-yl)-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (52 mg, 25%) as a yellow solid. 1H NMR (DMSO-d6): δ9.54 (s, 1H), 9.18 (s, 1H), 7.19 (d, J=2.01 Hz, 1H), 7.16 (s, 2H), 6.98 (s, 1H), 6.14 (t, J=3.02 Hz, 1H), 3.96 (s, 3H), 3.74 (s, 6H), 3.61 (s, 3H), 2.51 (s, 3H). MS m/z 394 (M+1).

Sources & evidence

ORD record
ord-245461025f094b31a642565a9ed32f6c
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

Loading…