Hydroxyamine hydrochloride → 4-Methyl-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-amine

HRID 1185200Notes

Reaction equation

HRID 1185200 reaction equation
CC1[N:3]([C:8]2[CH:17]=[C:11]3[CH:12]([CH3:16])[O:13][CH2:14][CH2:15][N:10]3[N:9]=2)C(C)=CC=1.Cl.NO>C(O)C>[CH3:16][CH:12]1[C:11]2=[CH:17][C:8]([NH2:3])=[N:9][N:10]2[CH2:15][CH2:14][O:13]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 866840502-(2,5-Dimethyl-1H-pyrrol-1-yl)-4-methyl-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazine

Product 1

HCID 866840524-Methyl-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-amineYield 8.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 100-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 150g (550 mg, 1.0 eq., 2.38 mmol), hydroxylamine hydrochloride (827 mg, 5.0 eq., 11.9 mmol), and ethanol (30 mL). The mixture was refluxed for 2 days. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by reverse-phase prep-HPLC to afford 150h (30 mg, 8%) as a yellow oil. MS-ESI: [M+H]+ 154.1. 1H NMR (500 MHz, CDCl3) δ 5.37 (s, 1H), 4.73 (q, J=7.0 Hz, 1H), 4.26-4.23 (m, 1H), 4.08-4.03 (m, 1H), 3.91-3.90 (m, 1H), 3.90-3.87 (m, 1H), 1.65 (d, J=7.0 Hz, 3H).

Workup

  1. customA 100-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. temperatureThe mixture was refluxed for 2 days
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-1838ac4e1b754a749e7b72fdd29aa754
Source dataset
uspto-grants-2014_03
Patent number
US08669251B2

Reaction notes

Loading…