Potassium Iodide → (2-propynyl)amino[methyl]-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine

HRID 596363Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH2:15]Cl)=[N:13][N:14]=[C:10]3[CH2:9][N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[C:6]=2[CH:24]=1.[CH2:25](N)[C:26]#[CH:27].[I-].[K+].C[N:32](C)C=O>>[CH2:27]([C:9]1([NH2:32])[N:8]=[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:6]2[CH:24]=[CH:2][CH:3]=[CH:4][C:5]=2[N:11]2[C:12]([CH3:15])=[N:13][N:14]=[C:10]12)[C:26]#[CH:25]

Participants

Reactant 4

HCID 4875Potassium Iodide

HCID 6228Dimethylformamide

HCID 239041Propargylamine

HCID 126123488-chloro-1-(chloromethyl)-6-(o-chlorophenyl)-4H-s-triazolo-[4,3-a][1,4]benzodiazepine

Product 1

HCID 86734530(2-propynyl)amino[methyl]-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Procedure

In the manner given in Preparation 19, 8-chloro-1-(chloromethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a]-[1,4]benzodiazepine in dimethylformamide is reacted at room temperature with propargylamine in the presence of potassium iodide to give 8-chloro-1-[[(2-propynyl)amino[methyl]-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine. Preparation 21 8-Fluoro-1-[[(2-propynyl)amino]methyl]-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Sources & evidence

ORD record: ord-7c2cc9f244c94cfcb38053e7517311c1
Source dataset: uspto-grants-1977_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04010177

Reaction notes

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