Hydrazine hydrate (1:1) → (2-Amino-ethyl)-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide

HRID 882927Notes

Reaction equation

[Br-:1].[NH2:2][C:3]1[C:4]([C:11]([NH:13][CH2:14][CH2:15][N+:16]([CH2:19][CH2:20][N:21]2C(=O)C3C(=CC=CC=3)C2=O)([CH3:18])[CH3:17])=[O:12])=[N:5][C:6]([Cl:10])=[C:7]([NH2:9])[N:8]=1.O.NN>CCO>[Br-:1].[NH2:21][CH2:20][CH2:19][N+:16]([CH2:15][CH2:14][NH:13][C:11]([C:4]1[C:3]([NH2:2])=[N:8][C:7]([NH2:9])=[C:6]([Cl:10])[N:5]=1)=[O:12])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of {2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-dimethyl-ammonium bromide (47 g, 92 mmol) and hydrazine monohydrate (20 mL, 412 mmol) in EtOH (500 mL) is heated at 40° C. for 4 h. After cooling to RT the resulting solid is removed by filtration and washed with diethyl ether. The filtrate is concentrated in vacuo to afford the title product. [M+H]+ 302.

Workup

temperatureAfter cooling to RT the resulting solid
customis removed by filtration
washwashed with diethyl ether
concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record: ord-96fd8fbeb6274be79460a30bd02fdd33
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236808B2

Reaction notes

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