Hydroxyamine hydrochloride → HCID 178428424, compound

HRID 218488Notes

Reaction equation

HRID 218488 reaction equation
[NH2:1][OH:2].Cl.[CH:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH:15]3[C:20]([C:21]#[N:22])=[C:19]([CH3:23])[NH:18][C:17]([CH3:24])=[C:16]3[C:25]#[N:26])[CH:13]=2)[NH:8][N:7]=1)=O>N1C=CC=CC=1>[OH:2]/[N:1]=[CH:4]/[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH:15]3[C:20]([C:21]#[N:22])=[C:19]([CH3:23])[NH:18][C:17]([CH3:24])=[C:16]3[C:25]#[N:26])[CH:13]=2)[NH:8][N:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 178428426HCID 178428426, compound

Product 1

HCID 178428424HCID 178428424, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of NH2OH.HCl (229 mg, 3.3 mmol) and 4-(3-formyl-1H-indazol-5-yl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile (200 mg, 0.66 mmol), from Synthetic Example 10B, in pyridine (5 mL) was stirred at rt overnight. After removal of pyridine under vacuum, the residue was treated with a saturated solution of NaHCO3 and extracted with CH2Cl2. The organic phases were combined, washed with brine, and concentrated. The residue was purified by column to give 1,4-dihydro-4-[3-[(E)-(hydroxyimino)methyl]-1H-indazol-5-yl]-2,6-dimethyl-3,5-pyridinedicarbonitrile (143 mg, 68%) as a powder (Cpd. No. 149, Table 2). 1H-NMR (400 MHz, DMSO-D6): δ=11.42 (s, 1H), 9.55 (s, 1H), 8.36 (s, 1H), 7.85 (s, 1H), 7.60 (d, 1H), 7.38 (d, 1H), 4.58 (s, 1H), 2.03 (s, 6H) ppm.

Workup

  1. customAfter removal of pyridine under vacuum
  2. additionthe residue was treated with a saturated solution of NaHCO3
  3. extractionextracted with CH2Cl2
  4. washwashed with brine
  5. concentrationconcentrated
  6. customThe residue was purified by column

Sources & evidence

ORD record
ord-4bc8924b6f794b4c96694d1ea2e0cfe2
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Reaction notes

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