Hydrazine hydrate (1:1) → 1-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine-6-carbohydrazonamide

HRID 456136Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([C:21]#[N:22])=[CH:19][N:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.O.[NH2:24][NH2:25]>CCO>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([C:21](=[N:24][NH2:25])[NH2:22])=[CH:19][N:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine-6-carbonitrile (80 mg, 0.278 mmol) in EtOH (3 mL), was added hydrazine hydrate (18.12 mg, 0.362 mmol). The reaction was heated to 60° C. overnight. The mixture was filtered and washed with EtOH, H2O, and EtOH to give a yellow solid. 1H-NMR (400 MHz, DMSO-d6+D2O) δ ppm 9.29 (s, 1H), 8.88 (s, 1H), 8.34 (d, 1H), 8.01 (m, 2H), 7.83 (d, 1H), 7.52 (m, 1H), 6.16 (s, 2H). LCMS (method B): [MH]+=320, tR=1.03 min.

Workup

filtrationThe mixture was filtered
washwashed with EtOH, H2O, and EtOH
customto give a yellow solid

Sources & evidence

ORD record: ord-469e1ae0be234654bbe99f59d67a7bbe
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497368B2

Reaction notes

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