4-(1H-imidazol-1-yl)aniline → 7-(3-{[4-(1H-imidazol-1-yl)phenyl]amino}phenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)-imidazo[5,1-f][1,2,4]triazin-2-amine

HRID 2374962Notes

Reaction equation

HRID 2374962 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:16]3[C:11]([CH:12]=[N:13][C:14]([NH:17][C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)=[N:15]3)=[C:10]([CH3:30])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[N:31]1([C:36]2[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=2)[CH:35]=[CH:34][N:33]=[CH:32]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+]>O1CCOCC1>[N:31]1([C:36]2[CH:42]=[CH:41][C:39]([NH:40][C:2]3[CH:3]=[C:4]([C:8]4[N:16]5[C:11]([CH:12]=[N:13][C:14]([NH:17][C:18]6[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=6)=[N:15]5)=[C:10]([CH3:30])[N:9]=4)[CH:5]=[CH:6][CH:7]=3)=[CH:38][CH:37]=2)[CH:35]=[CH:34][N:33]=[CH:32]1

Participants

6

Reactant 4

HCID 3201654-(1H-imidazol-1-yl)anilineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 112135557-(3-bromophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)-imidazo[5,1-f][1,2,4]triazin-2-amineHCID 23676156Sodium t-butoxide

Product 1

HCID 587119807-(3-{[4-(1H-imidazol-1-yl)phenyl]amino}phenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)-imidazo[5,1-f][1,2,4]triazin-2-amineYield 27%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a similar manner as described in Example 63, a mixture of 7-(3-bromophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (Example 9) (40 mg, 0.085 mmol), 4-(1H-imidazol-1-yl)aniline (13.5 mg, 0.085 mmol), 2-(dit-butylphosphino)biphenyl (15.2 mg, 0.051 mmol), Tris(dibenzylidineacetone)-dipalladium (0) (15.6 mg, 0.017 mmol) and sodium t-butoxide (13.1 mg, 0.136 mmol) in 1,4-dioxane (1.5 mL) gave 7-(3-{[4-(1H-imidazol-1-yl)phenyl]amino}phenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)-imidazo[5,1-f][1,2,4]triazin-2-amine (0.0126 g) as a yellow solid. 1H NMR (CDCl3): δ8.80 (s, 1H), 8.24 (s, 1H), 8.05 (d, J=7.3 Hz, 1H), 7.78 (s, 1H), 7.40-7.35 (m, 1H), 7.26-7.19 (m, 7H), 6.97-6.93 (s, 3H), 6.21 (s, 1H), 3.82 (s, 9H), 2.60 (s, 3H) MS m/z 549 (M+1).

Sources & evidence

ORD record
ord-a57edc01e6dd4aa48f0877ed8d4198bc
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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