Hydrochloric Acid → (S)-2-(1-Amino-3-(benzyloxy)propyl)-3-(3,5-difluorophenyl)-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazine-5-carbonitrile

HRID 1052365Notes

Reaction equation

HRID 1052365 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:32]C(=O)OC(C)(C)C)[C:12]1[N:17]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=2)[C:16](=[O:26])[C:15]2=[C:27]([C:30]#[N:31])[CH:28]=[CH:29][N:14]2[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O1CCOCC1>>[NH2:32][C@H:11]([C:12]1[N:17]([C:18]2[CH:19]=[C:20]([F:25])[CH:21]=[C:22]([F:24])[CH:23]=2)[C:16](=[O:26])[C:15]2=[C:27]([C:30]#[N:31])[CH:28]=[CH:29][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 131736115(S)-tert-Butyl (3-(benzyloxy)-1-(5-cyano-3-(3,5-difluorophenyl)-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate

Product 1

HCID 118433824(S)-2-(1-Amino-3-(benzyloxy)propyl)-3-(3,5-difluorophenyl)-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazine-5-carbonitrileYield 107.2%

Procedure

(S)-tert-Butyl (3-(benzyloxy)-1-(5-cyano-3-(3,5-difluorophenyl)-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)propyl)carbamate (50 mg, 0.09 mmol) was treated with a solution of hydrochloric acid in dioxane (4M, 350 μl, 1.4 mmol) according to the method described in Preparation 1 to obtain 42 mg (92% yield) of the title compound as a yellow solid. Purity 96%.

Workup

  1. customdescribed in Preparation 1

Sources & evidence

ORD record
ord-b7416a5ad60747ab989edb6d36e2325b
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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