Acetohydrazide → HCID 90010550, compound

HRID 1503298Notes

Reaction equation

HRID 1503298 reaction equation
[CH3:1][C:2]([N:7]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9]([CH3:15])=[N:8]1)([CH3:6])[C:3]([OH:5])=O.[C:16]([NH:19][NH2:20])(=[O:18])[CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:16]([NH:19][NH:20][C:3](=[O:5])[C:2]([CH3:1])([N:7]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9]([CH3:15])=[N:8]1)[CH3:6])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 14039AcetohydrazideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 19618577HCID 19618577, compound

Product 1

HCID 90010550HCID 90010550, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-methyl-2-(3-methyl-4-nitro-1H-pyrazol-1-yl)propanoic acid (500 mg, 2.38 mmol) in DCM (20 ml) was added acetohydrazide (211 mg, 2.86 mmol), HATU (1.8 g, 4.76 mmol), and DIPEA (618 mg, 4.76 mmol). The mixture was stirred at room temperature for 1 h. After concentration, the residue was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (1/3) to give the title product (600 mg, 95%) as light yellow oil. LC-MS (ESI): m/z=270.1 (M+H)+.

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by silica gel column chromatography
  3. washeluting with petroleum ether/ethyl acetate (1/3)

Sources & evidence

ORD record
ord-060a829ef5aa4b5f8fccc7bc208ffe03
Source dataset
uspto-grants-2015_12
Patent number
US09212173B2

Reaction notes

Loading…