Hydroxyamine hydrochloride → 4,5-Dimethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amine

HRID 593069Notes

Reaction equation

HRID 593069 reaction equation
CC1[N:3]([C:8]2[CH:18]=[C:11]3[CH:12]([CH3:17])[N:13]([CH3:16])[CH2:14][CH2:15][N:10]3[N:9]=2)C(C)=CC=1.NO.Cl>C(O)C>[CH3:17][CH:12]1[N:13]([CH3:16])[CH2:14][CH2:15][N:10]2[N:9]=[C:8]([NH2:3])[CH:18]=[C:11]12

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 866845282-(2,5-Dimethyl-1H-pyrrol-1-yl)-4,5-dimethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

Product 1

HCID 866845274,5-Dimethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amineYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 100-mL single-neck round-bottomed flask equipped with a reflux condenser was charged with 287h (1.63 g, 1.0 eq., 6.70 mmol), NH2OH.HCl (2.33 g, 5.0 eq., 33.5 mmol), and ethanol (50 mL). The mixture was refluxed for 2 days. It was then cooled to room temperature and concentrated under reduced pressure. The residue was purified by reverse-phase prep-HPLC to afford 287i as a yellow solid (211 mg, 19%). MS-ESI: [M+H]+ 167.1. 1H NMR (500 MHz, CDCl3) δ 5.36 (s, 1H), 4.04-4.00 (m, 1H), 3.94-3.92 (m, 1H), 3.61 (bs, 2H), 3.30 (q, J=6.5 Hz, 1H), 3.10-3.08 (m, 1H), 2.81-2.75 (m, 1H), 2.43 (s, 3H), 1.38 (d, J=6.5 Hz, 3H).

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a reflux condenser
  2. temperatureThe mixture was refluxed for 2 days
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-682942be54894829a2ac8c37c8daacb5
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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