Isopropylamine → HCID 86629464, compound

HRID 595384Notes

Reaction equation

HRID 595384 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([Cl:13])[CH:3]=1.[CH:14]([NH2:17])([CH3:16])[CH3:15].CCN(C(C)C)C(C)C>CC(N(C)C)=O>[Cl:13][C:4]1[CH:3]=[C:2]([NH:17][CH:14]([CH3:16])[CH3:15])[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylate

Product 1

HCID 86629464HCID 86629464, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A stirred solution of ethyl 4,6-dichloronicotinate (1) (10 g, 43.4 mmol), isopropyl amine (8 mL) and DIPEA (8 mL) in DMA (50 mL) were heated at 120° C. in a sealed tube for 3 h. The reaction mixture was concentrated to dryness to remove excess of DMA from the reaction mass. The crude material obtained was purified by column chromatography through silica gel and EtOAC: pet. Ether as eluent to obtain the title compound (2). LC/MS: Acquity BEH C18 2.1×50 mm, 1.8 micron; Solvent A=0.1% TFA in water; Solvent B=0.1% TFA in ACN; gradient 0-100% B over 2 min; retention time: 0.90 min; LCMS (ES-API), m/z 243.7 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customto remove excess of DMA from the reaction mass
  3. customThe crude material obtained
  4. customwas purified by column chromatography through silica gel and EtOAC

Sources & evidence

ORD record
ord-b90db7f3204247a7bca70997a6ea094d
Source dataset
uspto-grants-2016_01
Patent number
US09242975B2

Reaction notes

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