Ethyl chloroformate → HCID 57722938, compound

HRID 222287Notes

Reaction equation

HRID 222287 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6](=[O:21])[C:7]3[C:8]([CH:19]=[CH:20][C:4]=2[CH:3]=1)=[N:9][CH:10]=[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:12]=3.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[O:21]=[C:6]1[C:7]2[C:8](=[N:9][CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:12]=2)[CH:19]=[CH:20][C:4]2[CH:3]=[C:2]([NH:1][C:25](=[O:26])[O:27][CH2:28][CH3:29])[CH:23]=[CH:22][C:5]1=2

Participants

5

Reactant 2

HCID 10928Ethyl chloroformate3×HCID 15980909HCID 15980909, compound

Product 1

HCID 57722938HCID 57722938, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a 0° C. solution of 8-amino-3-phenyl-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (6.4 mg, 0.021 mmol) in pyridine (0.3 mL) was added a catalytic amount of 4-dimethylaminopyridine (tip of the spatula) and ethyl chloroformate (0.1 mL, 0.31 M in CH2Cl2) The mixture was then stirred at room temperature. After 7 hours, more ethyl chloroformate (3 μL, 0.032 mmol) was added. After stirring for 14 hours, a new addition of ethyl chloroformate (6 μL, 0.064 mmol) was followed by stirring for 2 more hours.

Workup

  1. stirringAfter stirring for 14 hours
  2. stirringby stirring for 2 more hours

Sources & evidence

ORD record
ord-4550c7a6784145ae9bc706195d2524c3
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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