1H-Indazole-5-carbonitrile → N-hydroxy-1H-indazole-5-carboximidamide

HRID 400733Notes

Reaction equation

HRID 400733 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:13]=[CH:12][C:8]2[NH:9]C=N[C:7]=2[CH:6]=1)[NH2:4].[NH:14]1[C:22]2C(=CC(C#N)=CC=2)C=N1>>[OH:1][N:2]=[C:3]([C:5]1[CH:6]=[C:7]2[C:8](=[CH:12][CH:13]=1)[NH:9][N:14]=[CH:22]2)[NH2:4]

Participants

3

Reactant 2

HCID 111263841H-Indazole-5-carbonitrileHCID 178513241N'-hydroxy-3H-benzimidazole-5-carboximidamide

Product 1

HCID 72532767N-hydroxy-1H-indazole-5-carboximidamide

Procedure

The title compound was prepared following procedure described for Intermediate 1, step 2, but starting from 1H-indazole-5-carbonitrile (JW-Pharmalab, 0.50 g; 3.49 mmol) as a beige solid (560 mg, 91%). 1H NMR (DMSO-d6) δ 13.12 (s, 1H), 9.54 (s, 1H), 8.10 (s, 1H), 8.04 (s, 1H), 7.71 (d, J=8.7 Hz, 1H), 7.49 (d, J=8.7 Hz, 1H), 5.82 (bs, 2H).

Sources & evidence

ORD record
ord-4e138912bab1469a89091263ce973bbe
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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