1H-1,2,4-Triazole → HCID 11364049, compound

HRID 2374893Notes

Reaction equation

HRID 2374893 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]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[C:19]([Cl:29])[CH:18]=2)=[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]=[CH:21][C:20]([N:23]5[CH2:28][CH2:27][O:26][CH2:25][CH2:24]5)=[C:19]([Cl:29])[CH:18]=4)=[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 58711988HCID 58711988, compound2×

Product 1

HCID 11364049HCID 11364049, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar manner as described for Example 9, 3-bromo-N-(1-{3-[(3-chloro-4-morpholin-4-ylphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide (Intermediate 24) (0.040 g, 0.080 mmol) and 1,2,4-triazole (35 mg, 0.50 mmol) in pyridine (1 mL) and phosphorus oxychloride (0.023 mL, 0.24 mmol) gave 7-(3-bromophenyl)-N-(3-chloro-4-morpholin-4-ylphenyl)-5-methylimidazo[5,1-f][1,2,4]triazin-2-amine (0.0089 g) as a yellow solid. 1H NMR (DMSO-d6): δ9.92 (s, 1H), 9.29 (s, 1H), 8.61 (dd, J=1.9, 1.8 Hz, 1H), 8.45 (ddd, J=8.1, 1.5, 1.1 Hz, 1H), 7.88 (d, J=2.5 Hz, 1H), 7.72 (dd, J=8.7, 2.6 Hz, 1H) 7.67 (ddd, J=8.1, 2.0, 1.0 Hz, 1H) 7.54 (dd, J=8.1, 7.8 Hz, 1H), 7.23 (d, J=9.0 Hz, 1H), 3.78-3.73 (m, 4H), 2.98-2.94 (m, 4H), 2.55 (s, 3H). MS m/z 499, 501 (M+1, M+3).

Sources & evidence

ORD record
ord-e40b887624f04fc0aa3b0a697cf11818
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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