Trifluoroacetic acid → (S)-2-(1-Aminoethyl)-5-((3-methoxyphenyl)thio)-3-phenyl pyrrol o[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052425Notes

Reaction equation

HRID 1052425 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9][C:10]2[CH:11]=[CH:12][N:13]3[C:18]=2[C:17](=[O:19])[N:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([C@@H:26]([NH:28]C(=O)OC(C)(C)C)[CH3:27])=[N:14]3)[CH:6]=[CH:7][CH:8]=1.FC(F)(F)C(O)=O>>[NH2:28][C@H:26]([C:15]1[N:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17](=[O:19])[C:18]2=[C:10]([S:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:11]=[CH:12][N:13]2[N:14]=1)[CH3:27]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736152(S)-tert-Butyl (1-(5-((3-methoxyphenyl)thio)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate

Product 1

HCID 118433878(S)-2-(1-Aminoethyl)-5-((3-methoxyphenyl)thio)-3-phenyl pyrrol o[2,1-f][1,2,4]triazin-4(3H)-oneYield 84.7%

Procedure

(S)-tert-Butyl (1-(5-((3-methoxyphenyl)thio)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate (154 mg, 0.31 mmol) was treated with trifluoroacetic acid (240 μl, 3.12 mmol) according to the method of Preparation 6 to obtain 103 mg (78% yield) of the title compound as an oil. Purity 92%.

Workup

  1. customaccording to the method of Preparation 6

Sources & evidence

ORD record
ord-7dc29d7f971648de8b28a01b39e9ade9
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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