Hydrochloric Acid → (S)-2-(1-Aminoethyl)-5-((2-hydroxyphenyl)thio)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052429Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:10]=[CH:11][N:12]2[C:17]=1[C:16](=[O:18])[N:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:14]([C@@H:25]([NH:27]C(=O)OC(C)(C)C)[CH3:26])=[N:13]2.Cl.O1CCOCC1>>[NH2:27][C@H:25]([C:14]1[N:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16](=[O:18])[C:17]2=[C:9]([S:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[OH:1])[CH:10]=[CH:11][N:12]2[N:13]=1)[CH3:26]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 131736153(S)-tert-Butyl (1-(5-((2-hydroxyphenyl)thio)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate

Product 1

HCID 118433855(S)-2-(1-Aminoethyl)-5-((2-hydroxyphenyl)thio)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 154.5%

Procedure

(S)-tert-Butyl (1-(5-((2-hydroxyphenyl)thio)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate (252 mg, 0.33 mmol) was treated with a solution of hydrochloric acid in dioxane (4M, 2 mL, 8 mmol) according to the method described in Preparation 1 to obtain 193 mg (99% yield) of the title compound. Purity 99%.

Workup

customdescribed in Preparation 1

Sources & evidence

ORD record: ord-c3dc4bac8db34c579366bb6c1ef9b41b
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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