Ethyl chloroformate → HCID 59850168, compound

HRID 2064172Notes

Reaction equation

HRID 2064172 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([Br:12])=[CH:4][C:3]=1[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.C(N(C(C)C)CC)(C)C.Cl[C:37](OCC)=[O:38]>O1CCCC1.CN(C)C=O>[Br:12][C:5]1[C:6]([C:8]([F:11])([F:9])[F:10])=[CH:7][C:2]2[NH:1][C:37](=[O:38])[N:13]([CH:14]3[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]3)[C:3]=2[CH:4]=1

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 59850178HCID 59850178, compound

Product 1

HCID 59850168HCID 59850168, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 1,1-dimethylethyl 4-{[2-amino-5-bromo-4-(trifluoromethyl)phenyl]amino}-1-piperidinecarboxylate (D67, 0.98 g, 2.2 mmol) in tetrahydrofuran (25 ml) at room temperature under argon was treated with diisopropylethylamine (0.78 ml, 4.4 mmol) followed by ethyl chloroformate (0.24 ml, 2.5 mmol) and maintained for 20 hrs. The solution was concentrated under vacuum and the residue treated with 10% Na2CO3 solution and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated under vacuum to leave a beige solid, which was dissolved in dimethylformamide (20 ml) and heated with stirring under argon for 1.5 hrs. The mixture was concentrated under vacuum and the residue treated with 10% Na2CO3 solution and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated under vacuum to afford the title compound as a light brown solid (0.95 g, 91%).

Workup

  1. temperaturemaintained for 20 hrs
  2. concentrationThe solution was concentrated under vacuum
  3. additionthe residue treated with 10% Na2CO3 solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried (Na2SO4)
  6. concentrationconcentrated under vacuum
  7. customto leave a beige solid, which
  8. temperatureheated
  9. concentrationThe mixture was concentrated under vacuum
  10. additionthe residue treated with 10% Na2CO3 solution
  11. extractionextracted with ethyl acetate
  12. dry with materialThe extract was dried (Na2SO4)
  13. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2a53078e067843ac813f08fbfab7a79f
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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