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

HRID 2063270Notes

Reaction equation

HRID 2063270 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.C(N)C.[Cl:24]CCCl>>[C:1]([O:5][C:6](=[O:7])[N:8]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([Cl:24])=[O:14])=[CH:11][N:10]=1)[CH3:18])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 6341EthylamineHCID 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-05 using methylamine in stead 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-e8c22a70c07443e499cf9bd59d47ddc2
Source dataset
uspto-grants-2012_10
Patent number
US08288379B2

Reaction notes

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