1H-1,2,4-Triazole → HCID 11785354, compound

HRID 2374891Notes

Reaction equation

HRID 2374891 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[C:5]([NH:7][CH:8]([C:10]1[N:15]=[N:14][C:13]([NH:16][C:17]2[CH:22]=[C:21]([S:23]([CH2:26][CH3:27])(=[O:25])=[O:24])[CH:20]=[CH:19][C:18]=2[O:28][CH3:29])=[N:12][CH:11]=1)[CH3:9])=O.N1C=NC=N1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[N:15]3[C:10]([CH:11]=[N:12][C:13]([NH:16][C:17]4[CH:22]=[C:21]([S:23]([CH2:26][CH3:27])(=[O:25])=[O:24])[CH:20]=[CH:19][C:18]=4[O:28][CH3:29])=[N:14]3)=[C:8]([CH3:9])[N:7]=2)[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 587120043-bromo-N-[1-(3-{[5-(ethylsulfonyl)-2-methoxyphenyl]amino}-1,2,4-triazin-6-yl)ethyl]benzamide2×

Product 1

HCID 11785354HCID 11785354, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar manner as described for Example 9, 3-bromo-N-[1-(3-{[5-(ethylsulfonyl)-2-methoxyphenyl]amino}-1,2,4-triazin-6-yl)ethyl]benzamide (Intermediate 23) (0.11 g, 0.20 mmol) and 1,2,4-triazole (83 mg, 1.2 mmol) in pyridine (2 mL) and phosphorus oxychloride (0.056 mL, 0.6 mmol) gave 7-(3-bromophenyl)-N-[5-(ethylsulfonyl)-2-methoxyphenyl]-5-methylimidazo[5,1-f][1,2,4]triazin-2-amine (0.028 g) as a yellow solid. 1H NMR (CDCl3): δ8.89 (d, J=2.2 Hz, 1H), 8.85 (s, 1H), 8.69-8.60 (m, 1H), 8.43 (dd, J=1.8, 1.8 Hz, 1H), 7.81-7.75 (m, 2H), 7.63 (dd, J=8.5, 2.3 Hz, 1H), 7.58 (ddd, J=7.9, 2.0, 1.0 Hz, 1H), 7.04 (d, J=8.6 Hz, 1H), 4.04 (s, 3H), 3.06 (q, J=7.4 Hz, 2H), 2.63 (s, 3H), 1.23 (t, J=7.4 Hz, 3H). MS m/z 502, 504 (M+1, M+3).

Sources & evidence

ORD record
ord-7253e9f1af8e4152b0ffa43eac456478
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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