1-(5-amino-2,3-dihydro-1H-indol-1-yl)ethan-1-one → N-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine

HRID 2375017Notes

Reaction equation

HRID 2375017 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.[C:39]([N:42]1[C:50]2[C:45](=[CH:46][C:47]([NH2:51])=[CH:48][CH:49]=2)[CH2:44][CH2:43]1)(=[O:41])[CH3:40]>C(O)C>[C:39]([N:42]1[C:50]2[C:45](=[CH:46][C:47]([NH:51][C:7]3[N:8]=[CH:9][C:10]4=[C:2]([CH3:1])[N:3]=[C:4]([C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=5)[N:5]4[N:6]=3)=[CH:48][CH:49]=2)[CH2:44][CH2:43]1)(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 2925071-(5-amino-2,3-dihydro-1H-indol-1-yl)ethan-1-oneHCID 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 11451932N-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amineYield 30.6%

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), 1-acetyl-5-amino-2,3-dihydro-(1h)-indole (30.5 mg, 0.17 mmol) and ethanol (2.5 mL) to afford N-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine (20 mg) as a yellow solid. MS m/z 385 (M+1).

Sources & evidence

ORD record
ord-ac7d417c732b4643bd2ff358b317c6d9
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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