Triethylamine → HCID 56943059, compound

HRID 467993Notes

Reaction equation

HRID 467993 reaction equation
COC(=O)[CH:4]([CH:24]1CC1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([CH:21]1[CH2:23][CH2:22]1)C(O)=O.[C:28](Cl)(=[O:32])C(Cl)=O.C(N(CC)CC)C.[CH:41]1([NH2:44])[CH2:43][CH2:42]1.[C:45]([O:48][CH2:49]C)(=[O:47])C>ClCCl.CN(C=O)C>[CH3:49][O:48][C:45]([C:21]1([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]2([C:28](=[O:32])[NH:44][CH:41]3[CH2:43][CH2:42]3)[CH2:4][CH2:24]2)[CH2:22][CH2:23]1)=[O:47]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 65578Oxalyl chlorideHCID 69828CyclopropylamineHCID 66795678HCID 66795678, compound

Product 1

HCID 56943059HCID 56943059, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of product of Example 33 (0.91 g, 2.58 mmol) in dichloromethane (9.1 mL) was added oxalyl chloride (0.4 mL, 5.1 mmol) and catalytic amount of DMF (0.015 mL) at ice temperature. The ice bath was removed and reaction mixture stirred at room temperature over a period of 1 h. The crude product obtained upon evaporation of the solvent was diluted with DCM (10 mL), cooled to ice bath temperature added triethyl amine (1.0 mL, 7.75 mmol), and cyclopropyl amine (1.04 g, 2.5 mmol) added in a drop wise fashion. Then reaction mixture was slowly allowed to reach room temperature and stirred for 16 h. The resulting reaction mass was diluted with ethyl acetate (250 mL), washed with water (50 mL) and dried over sodium sulphate. The residue obtained upon evaporation of the volatiles was purified by silica gel (230-400) column (25% ethyl acetate in petroleum ether) to give product as an off-white solid 0.79 g (79%). mp: 50.6° C.-53.0° C.

Workup

  1. customThe ice bath was removed
  2. customreaction mixture
  3. customThe crude product obtained upon evaporation of the solvent
  4. temperaturecooled to ice bath temperature
  5. additionadded in a drop wise fashion
  6. customThen reaction mixture
  7. customto reach room temperature
  8. stirringstirred for 16 h
  9. customThe resulting reaction mass
  10. washwashed with water (50 mL)
  11. dry with materialdried over sodium sulphate
  12. customThe residue obtained upon evaporation of the volatiles
  13. customwas purified by silica gel (230-400) column (25% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-67a9f8568f214d2f9d57b8f91d57b638
Source dataset
uspto-grants-2014_01
Patent number
US08623897B2

Reaction notes

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