Hydroxyamine hydrochloride → HCID 178513336, compound

HRID 499146Notes

Reaction equation

HRID 499146 reaction equation
[Na].Cl.[NH2:3][OH:4].[F:5][C:6]([F:30])([F:29])[C:7]1[CH:28]=[CH:27][CH:26]=[CH:25][C:8]=1[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:22]=[N:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:10]>C(O)C>[OH:4][NH:3][C:23]([C:20]1[N:21]=[N:22][C:17]([N:14]2[CH2:13][CH2:12][N:11]([C:9](=[O:10])[C:8]3[CH:25]=[CH:26][CH:27]=[CH:28][C:7]=3[C:6]([F:30])([F:29])[F:5])[CH2:16][CH2:15]2)=[CH:18][CH:19]=1)=[NH:24]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 5360545Sodium2×HCID 675233306-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carbonitrile

Product 1

HCID 178513336HCID 178513336, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium metal (0.116 g, 4.98 mmol) was added to ice cold ethanol (10 mL). When all the sodium metal dissolved, hydroxylamine hydrochloride (0.346 g, 4.98 mmol) was introduced in one portion. The suspension was stirred at room temperature for 15 minutes and a solution of 6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]-pyridazine-3-carbonitrile (0.900 g, 2.49 mmol) in ethanol (2 mL) was then added. The mixture was further stirred at room temperature overnight. The solvent was removed in vacuo and the residue was suspended in ethyl acetate (10 mL) and filtered through celite. The filtrate was concentrated and the product was purified by column chromatography. The title compound was obtained as a pale yellow syrup in 55% yield (0.54 g). 1H NMR (300 MHz, CDCl3) δ 7.82 (d, J=9.6 Hz, 1H), 7.45 (d, J=7.6 Hz, 1H), 7.70-7.52 (m, 2H), 7.35 (d, J=7.4 Hz, 1H), 6.95 (d, J=9.5 Hz, 1H), 5.53 (s, 2H), 4.10-3.95 (m, 1H), 3.98-3.82 (m, 1H), 3.82-3.60 (m, 4H), 3.32 (t, J=5.1 Hz, 2H). 13C NMR (75 MHz, CDCl3) δ 157.5, 147.5, 142.1, 132.2, 130.2, 127.3, 125.1, 123.2, 110.8, 44.2, 42.6, 42.3, 39.1 MS (ES+) m/z 395.3 (M+H).

Workup

  1. stirringThe mixture was further stirred at room temperature overnight
  2. customThe solvent was removed in vacuo
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated
  5. customthe product was purified by column chromatography

Sources & evidence

ORD record
ord-e1fc8326ec364006aa5ef65d4acb1296
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

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