Isopropylamine → HCID 43510674, compound

HRID 62822Notes

Reaction equation

HRID 62822 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH:12]([N:15](C(C)C)CC)([CH3:14])[CH3:13].C(N)(C)C>C(#N)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([NH:15][CH:12]([CH3:14])[CH3:13])=[O:9]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 27359105-Amino-2-fluorobenzoic acid

Product 1

HCID 43510674HCID 43510674, compoundYield 619.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-amino-2-fluorobenzoic acid (300 mg, 1.9 mmol), diisopropylethylamine (1 ml, 5.8 mmol), and isopropylamine (0.3 ml, 3.9 mmol) in acetonitrile was heated to 110° C. in microwave for 45 min. This reaction was repeated 5 times and the crude products combined then concentrated in vacuo. The residue was purified by flash chromatography (SiO2) eluting with ethyl acetate/dichloromethane (0% to 10% v/v) to afford the title compound as a yellow solid (2.31 g). HPLC retention time 3.93 min. Mass spectrum (ES+) m/z 197 (M+H).

Workup

  1. concentrationthe crude products combined then concentrated in vacuo
  2. customThe residue was purified by flash chromatography (SiO2)
  3. washeluting with ethyl acetate/dichloromethane (0% to 10% v/v)

Sources & evidence

ORD record
ord-7feac0f33c2d4018b8429d8d04e9abb0
Source dataset
uspto-grants-2016_09
Patent number
US09447033B2

Reaction notes

Loading…