3-(2-Morpholin-4-ylethoxy)aniline → 5-methyl-N-(3-{[2-(4-morpholinyl)ethyl]oxy}phenyl)-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine

HRID 2375021Notes

Reaction equation

HRID 2375021 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7](SC)=[N:6]2.CC1N=C(C2C=CC=CC=2)N2C=1C=NC(S(C)(=O)=O)=N2.[N:39]1([CH2:45][CH2:46][O:47][C:48]2[CH:49]=[C:50]([NH2:54])[CH:51]=[CH:52][CH:53]=2)[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>C(O)C>[CH3:1][C:2]1[N:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([NH:54][C:50]1[CH:51]=[CH:52][CH:53]=[C:48]([O:47][CH2:46][CH2:45][N:39]3[CH2:40][CH2:41][O:42][CH2:43][CH2:44]3)[CH:49]=1)=[N:6]2

Participants

5

Reactant 3

HCID 64866163-(2-Morpholin-4-ylethoxy)anilineHCID 534718325-Methyl-2-(methylthio)-7-phenylimidazo[5,1-F][1,2,4]triazineHCID 534718335-Methyl-2-(methylsulfonyl)-7-phenylimidazo[5,1-F][1,2,4]triazine

Product 1

HCID 114759265-methyl-N-(3-{[2-(4-morpholinyl)ethyl]oxy}phenyl)-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amineYield 24.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Applying the displacement procedure, using 5-methyl-2-(methylthio)-7-phenylimidazo[5,1-f][1,2,4]triazine (Intermediate 72) (50 mg, 0.17 mmol), (3-{[2-(4-morpholinyl)ethyl]oxy}phenyl)amine (38 mg, 0.17 mmol) and ethanol (2.5 mL) to afford 5-methyl-N-(3-{[2-(4-morpholinyl)ethyl]oxy}phenyl)-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine (18 mg) as a yellow solid. MS m/z 431 (M+1).

Sources & evidence

ORD record
ord-5a2bf839a9d1462ab2acc975c24ee2b1
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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