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

HRID 1052435Notes

Reaction equation

HRID 1052435 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:10][C:11]2[CH:12]=[CH:13][N:14]3[C:19]=2[C:18](=[O:20])[N:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([C@@H:27]([NH:29]C(=O)OC(C)(C)C)[CH3:28])=[N:15]3)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl.O1CCOCC1>>[NH2:29][C@H:27]([C:16]1[N:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18](=[O:20])[C:19]2=[C:11]([S:10][C:4]3[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=3)[CH:12]=[CH:13][N:14]2[N:15]=1)[CH3:28]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131736157(S)-tert-Butyl (1-(5-((3-fluoro-4-methoxyphenyl)thio)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate

Product 1

HCID 118433749(S)-2-(1-Aminoethyl)-5-((3-fluoro-4-methoxyphenyl)thio)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 98%

Procedure

(S)-tert-Butyl (1-(5-((3-fluoro-4-methoxyphenyl)thio)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate (226 mg, 0.44 mmol) was treated with a solution of hydrochloric acid in dioxane (4M, 2.2 mL, 8.8 mmol) according to the method described in Preparation 1 to obtain 293 mg (95% purity, 98% yield) of the title compound as a hydrochloride salt that was used in the following step without further purification.

Workup

  1. customdescribed in Preparation 1

Sources & evidence

ORD record
ord-03a2b71e8a0545b98447703396a8938c
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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