1-Chloroethyl chloroformate → HCID 66734806, compound

HRID 1441494Notes

Reaction equation

HRID 1441494 reaction equation
C([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][N:9]=[C:10]([C:15]3[CH:16]=[N:17][C:18]([CH:21]4[CH2:23][CH2:22]4)=[N:19][CH:20]=3)[CH:11]=2)[CH2:6]1)(C)(C)C.[Cl:24]C(OC(Cl)C)=O.[Cl-].[Ca+2].[Cl-]>C1(C)C=CC=CC=1>[ClH:24].[CH:21]1([C:18]2[N:19]=[CH:20][C:15]([C:10]3[CH:11]=[C:12]4[C:7](=[CH:8][N:9]=3)[CH2:6][NH:5][CH2:14][CH2:13]4)=[CH:16][N:17]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 5213051-Chloroethyl chloroformateHCID 5284359Calcium ChlorideHCID 66733948HCID 66733948, compound

Product 1

HCID 66734806HCID 66734806, compoundYield 106.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-tert-butyl-6-(2-cyclopropylpyrimidin-5-yl)-1,2,3,4-tetrahydro-2,7-naphthyridine (0.12 g, 0.39 mmol), 1-chloroethyl chloroformate (1.0 mL, 5.8 mmol) and toluene (10 mL) was refluxed for 4 h under protection from moisture (calcium chloride tube). After concentration to dryness, the dark residue was taken up in MeOH (10 mL) and refluxed for 3 h more. Charcoal (1 g) was added and refluxing continued for 20 minutes. Then the mixture was filtered through Celite and the clear filtrate was concentrated to give the title compound (0.12 g) as a solid.

Workup

  1. concentrationAfter concentration to dryness
  2. temperaturerefluxed for 3 h more
  3. additionCharcoal (1 g) was added
  4. temperaturerefluxing
  5. filtrationThen the mixture was filtered through Celite
  6. concentrationthe clear filtrate was concentrated

Sources & evidence

ORD record
ord-fcd4105fd95e4c94b02b8ed8e5185303
Source dataset
uspto-grants-2010_02
Patent number
US07655664B2

Reaction notes

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