Dichloromethane → tert-butyl N-[[(2-chloro-4-pyridinyl)amino]-[(2-methylpropan-2-yl)oxycarbonylamino]methylidene]carbamate

HRID 2389562Notes

Reaction equation

HRID 2389562 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:8])[CH:3]=1.ClCCl.[C:12]([NH:19][C:20](=[N:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])SC)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>C(N(CC)CC)C.[Hg](Cl)Cl>[C:27]([O:26][C:24](=[O:25])[NH:23]/[C:20](/[NH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:8])[CH:3]=1)=[N:19]\[C:12](=[O:13])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 844322-Chloropyridin-4-amineHCID 5466031,3-DI-Boc-2-methylisothiourea

Product 1

HCID 178454301tert-butyl N-[[(2-chloro-4-pyridinyl)amino]-[(2-methylpropan-2-yl)oxycarbonylamino]methylidene]carbamateYield 75%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 8471TriethylamineSolvent

Procedure

20.22 g (0.157 mol) of 4-amino-2-chloropyridine were diluted in triethylamine (67 ml) and dichloromethane (600 ml) at 0-5° C. 47 g of Mercury(II) chloride (0.173 mol) and 50.24 g (0.173 mol) of N,N′-bis(boc)-S-methyl-isothiourea were added to the reaction mixture, which was then stirred at room temperature for 4 days, filtered on a fritted funnel, concentrated in vacuo and chromatographed on silica (Heptane90/AcOEt10) to yield 43.67 g of di-tert-butyl{(Z)-[(2-chloropyridin-4-yl)amino]methylylidene}biscarbamate (yield=71%).

Workup

  1. customat 0-5° C
  2. filtrationfiltered on a fritted funnel
  3. concentrationconcentrated in vacuo
  4. customchromatographed on silica (Heptane90/AcOEt10)

Sources & evidence

ORD record
ord-1cb60982877d46f684d987b41863eb84
Source dataset
uspto-grants-2012_09
Patent number
US08273759B2

Reaction notes

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