Ethyl (chloroformyl)acetate → HCID 86717889, compound

HRID 2275778Notes

Reaction equation

HRID 2275778 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=1.Cl[CH:19]([CH:25]=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][N:12]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 118030Ethyl (chloroformyl)acetate2×HCID 102634983-(2,6-Difluoro-benzyloxy)-pyridin-2-ylamine

Product 1

HCID 86717889HCID 86717889, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.93 g of 3-[(2,6-difluorobenzyl)oxy]pyridine-2-amine (Example 1A; 8.2 mmol, 1 equivalent) were initially charged in 50 ml of ethanol, and 8.2 g of ethyl 2-chloro-3-oxopropanoate (75% pure, crude product from Example 26A, 40.8 mmol, 5 equivalents) were added. The reaction mixture was heated at reflux overnight. The mixture was then concentrated under reduced pressure and the crude product obtained was chromatographed on 340 g of silica gel (Biotage Isolera) (mobile phase: cyclohexane:ethyl acetate gradient; Rf value of the product in cyclohexane:ethyl acetate 2:1=0.36). The product fractions were combined and concentrated and the residue obtained was triturated with diisopropyl ether. The solid was filtered off and dried under high vacuum. This gave 2.02 g of the title compound (71% of theory).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-05d6a94b510243a0a46172869e5964ac
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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