Ammonium → 3-{5-Methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}benzamide

HRID 2374894Notes

Reaction equation

HRID 2374894 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:24]2[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=2)[C:27]([O:29]C)=O)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([NH:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1)=[N:6]2.[NH4+:34]>CO>[CH3:1][C:2]1[N:3]=[C:4]([C:24]2[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=2)[C:27]([NH2:34])=[O:29])[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([NH:11][C:12]1[CH:13]=[C:14]([O:22][CH3:23])[C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=1)=[N:6]2

Participants

4

Reactant 2

HCID 223AmmoniumHCID 11775266Methyl 3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}benzoate

Product 1

HCID 111547673-{5-Methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl 3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}benzoate (Example 12) (0.020 g, 0.044 mmol) was added 7N ammonium in methanol (5 mL). The solution was heated in a sealed tube for 18 hours. After cooling to room temperature, the volatiles were removed under reduced pressure to give 3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}benzamide (0.015 g) as a yellow solid. 1H NMR (CDCl3): δ9.41 (s, 1H), 9.16 (s, 1H), 8.73 (d, J=7.3 Hz, 1H), 8.27 (d, J=7.6 Hz, 1H), 8.23-8.17 (m, 1H), 7.75-7.59 (m, 3H) 7.26 (s, 2H), 3.98 (s, 3H), 3.92 (s, 3H), 3.72 (s, 3H), 2.71 (s, 3H). MS m/z 435 (M+1).

Workup

  1. temperatureThe solution was heated in a sealed tube for 18 hours
  2. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-39075325e5a64bcf921ea3cca478382c
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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