1,2-Dichloroethane → (5-Chlorocarbonyl-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester

HRID 595089Notes

Reaction equation

HRID 595089 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:18])[C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN.[Cl:21]CCCl>>[C:1]([O:5][C:6](=[O:7])[N:8]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([Cl:21])=[O:14])=[CH:11][N:10]=1)[CH3:18])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 667695966-((tert-Butoxycarbonyl)(methyl)amino)nicotinic acid

Product 1

HCID 86664608(5-Chlorocarbonyl-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester

Procedure

6-(tert-Butoxycarbonyl-methyl-amino)-nicotinic acid (12.5 g, 47.0 mmol) (prepared analogously to A-08 using methyl amine instead of ethylamine) is taken up in 300 mL DCE, 1-chloro-N,N-2-trimethylpropenyl-amine (10.0 mL, 74.8 mmol) is added and the reaction mixture is stirred overnight at RT. The reaction mixture is concentrated under reduced pressure and the crude product is used in the next step without purification.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe crude product is used in the next step without purification

Sources & evidence

ORD record
ord-bf3d18c3d7cf4427a65888a6a7e7691e
Source dataset
uspto-grants-2016_01
Patent number
US09243000B2

Reaction notes

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