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

HRID 1052444Notes

Reaction equation

HRID 1052444 reaction equation
[CH3:1][N:2]([CH3:39])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12][C:13]1[CH:14]=[CH:15][N:16]2[C:21]=1[C:20](=[O:22])[N:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18]([C@@H:29]([NH:31]C(=O)OC(C)(C)C)[CH3:30])=[N:17]2.Cl.O1CCOCC1>>[NH2:31][C@H:29]([C:18]1[N:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20](=[O:22])[C:21]2=[C:13]([S:12][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[NH:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:39])[CH:14]=[CH:15][N:16]2[N:17]=1)[CH3:30]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131736158HCID 131736158, compound

Product 1

HCID 118433892(S)-2-(1-Aminoethyl)-5-((2-((2-(dimethylamino)ethyl)amino)phenyl)thio)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 63%

Procedure

(S)-tert-Butyl (1-(5-((2-((2-(dimethylamino)ethyl)amino)phenyl)thio)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate (432 mg, 0.79 mmol) was treated with a solution of hydrochloric acid in dioxane (4M, 3.9 mL, 15.76 mmol) according to the method described in Preparation 1 to obtain 267 mg (90% purity, 63% 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-bdc15cee4228443cbf496cac29569100
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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