1-Chloroethyl chloroformate → HCID 118023935, compound

HRID 2171820Notes

Reaction equation

HRID 2171820 reaction equation
C([N:8]1[CH2:13][CH:12]2[CH2:14][CH2:15][CH:9]1[C:10](=[O:33])[N:11]2[CH2:16][C:17]1[C:18]2[CH:26]=[C:25]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[S:24][C:19]=2[N:20]=[C:21]([CH3:23])[N:22]=1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[CH:27]1([C:25]2[S:24][C:19]3[N:20]=[C:21]([CH3:23])[N:22]=[C:17]([CH2:16][N:11]4[C:10](=[O:33])[CH:9]5[CH2:15][CH2:14][CH:12]4[CH2:13][NH:8]5)[C:18]=3[CH:26]=2)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 118024028HCID 118024028, compound

Product 1

HCID 118023935HCID 118023935, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 5-benzyl-2-[(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl]-2,5-diazabicyclo[2.2.2]octan-3-one (140 mg) and DCE (5 mL) was added 1-chloroethyl chloroformate (50 μL), followed by stirring at room temperature overnight. The reaction solution was purified by silica gel column (chloroform/MeOH/saturated aqueous NH3) without concentration. The residue was dissolved in MeOH, and heated to reflux for 30 minutes. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column (chloroform/MeOH/saturated aqueous NH3) to obtain 2-[(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methyl]-2,5-diazabicyclo[2.2.2]octan-3-one (87 mg).

Workup

  1. customThe reaction solution was purified by silica gel column (chloroform/MeOH/saturated aqueous NH3) without concentration
  2. dissolutionThe residue was dissolved in MeOH
  3. temperatureheated
  4. temperatureto reflux for 30 minutes
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column (chloroform/MeOH/saturated aqueous NH3)

Sources & evidence

ORD record
ord-23df4249bd4d4e7195ad4fb50769ee47
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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