Hydrochloric Acid → (S)-2-(1-Amino-3-(benzyloxy)propyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052395Notes

Reaction equation

HRID 1052395 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:29]C(=O)OC(C)(C)C)[C:12]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16](=[O:24])[C:15]2=[C:25]([CH3:28])[CH:26]=[CH:27][N:14]2[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O1CCOCC1>>[NH2:29][C@H:11]([C:12]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16](=[O:24])[C:15]2=[C:25]([CH3:28])[CH:26]=[CH:27][N:14]2[N:13]=1)[CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131736131(S)-tert-Butyl (3-(benzyloxy)-1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate

Product 1

HCID 118433815(S)-2-(1-Amino-3-(benzyloxy)propyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 103%

Procedure

(S)-tert-Butyl (3-(benzyloxy)-1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate (30 mg, 0.06 mmol) was treated with a solution of hydrochloric acid in dioxane (4M, 230 μl, 0.92 mmol) according to the method described in Preparation 1 to obtain 24 mg (91% yield) of the title compound. Purity 98%.

Workup

  1. customdescribed in Preparation 1

Sources & evidence

ORD record
ord-e06e18a60e47442882c11722008b82ea
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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