6-Hydrazinylnicotinonitrile → HCID 46174985, compound

HRID 1925109Notes

Reaction equation

HRID 1925109 reaction equation
[NH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=1)[NH2:2].BrC1C=CC2N([C:18]([S:21][C:22]3[CH:23]=[CH:24][C:25]4[N:26]([CH:28]=[C:29]([NH:31][C:32]([CH:34]5[CH2:36][CH2:35]5)=[O:33])[N:30]=4)[N:27]=3)=NN=2)C=1>>[C:7]([C:6]1[CH:9]=[CH:10][C:3]2[N:4]([C:18]([S:21][C:22]3[CH:23]=[CH:24][C:25]4[N:26]([CH:28]=[C:29]([NH:31][C:32]([CH:34]5[CH2:36][CH2:35]5)=[O:33])[N:30]=4)[N:27]=3)=[N:2][N:1]=2)[CH:5]=1)#[N:8]

Participants

3

Reactant 2

HCID 5841956-HydrazinylnicotinonitrileHCID 46174984N-(6-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-ylthio)imidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide

Product 1

HCID 46174985HCID 46174985, compound

Procedure

To a suspended mixture of 6-chloronicotinonitrile (7 g, 50.8 mmol) in EtOH (50 mL), was added NH2NH2 (10 g, 310.2 mmol). The mixture was stirred at room temperature for 10 min, and then 60° C. for 5 h. The mixture was cooled to room temperature. The solids were filtered out, washed with water and dried under high vacuum to give 6-hydrazinylnicotinonitrile (3.5 g). Compound 6 was prepared from 6-hydrazinylnicotinonitrile following the procedure of the synthesis of compound 4. 1H NMR (400 MHz, CDCl3-CD3OD 10:1) δ ppm 11.37 (s, 1H), 8.70 (t, J=1.2 Hz, 1 H), 8.14 (s, 1 H), 8.11(dd, J=1.04 and 9.52 Hz, 1 H), 7.96 (dd, J=1.12 and 9.52 Hz, 1 H), 7.61 (dd, J=1.52 and 9.48 Hz, 1 H), 7.38 (d, J=9.0 Hz, 1 H), 1.77 (m, 1 H), 1.06 (m, 2 H), 0.90 (m, 2H) ESI-MS:m/z 377.2 (M+H)+.

Sources & evidence

ORD record
ord-5d37a27d877a4ff5a54d8e0fc471f26f
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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