5-Aminoisoxazole → HCID 178428416, compound

HRID 1521788Notes

Reaction equation

HRID 1521788 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8](/[CH:11]=[C:12](/[C:14](=O)[CH3:15])\[CH3:13])[CH:9]=2)[NH:4][N:3]=1.[N:17]([O-])=O.[O:20]1[C:24]([NH2:25])=[CH:23][CH:22]=[N:21]1>CC(O)C>[CH3:15][C:14]1[NH:25][C:24]2[O:20][N:21]=[CH:22][C:23]=2[CH:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][N:3]=[C:2]3[CH3:1])[C:12]=1[C:13]#[N:17]

Participants

4

Reactant 2

HCID 845915-AminoisoxazoleHCID 178467756HCID 178467756, compound

Product 1

HCID 178428416HCID 178428416, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 50 mg (0.22 mmol) (2E)-2-[(3-methyl-1H-indazol-5-yl)methylidene]-3-oxobutane-nitrite (Example 2A) and 19 mg (0.22 mmol) 1,2-oxazol-5-amine in propan-2-ol (1.0 ml) was stirred at reflux temperature overnight. The reaction mixture was then concentrated under reduced pressure, and the residue was purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient) to yield 45 mg (69% of th.) of the racemic title compound.

Workup

  1. temperatureat reflux temperature overnight
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customthe residue was purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA gradient)

Sources & evidence

ORD record
ord-27355b7a089b476a8742c2f21cbef120
Source dataset
uspto-grants-2015_07
Patent number
US09073939B2

Reaction notes

Loading…