Methyl chloroformate → HCID 11592247, compound

HRID 577796Notes

Reaction equation

HRID 577796 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]([F:42])([F:41])[C:9]1[CH:10]=[C:11]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH2:12][NH:13][CH2:14][C:15]1[C:16]([N:25]([CH2:28][CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:26][CH3:27])=[N:17][C:18]2[CH2:19][CH2:20][CH2:21][CH2:22][C:23]=2[CH:24]=1.Cl[C:44]([O:46][CH3:47])=[O:45]>C1COCC1>[CH3:47][O:46][C:44](=[O:45])[N:13]([CH2:12][C:11]1[CH:10]=[C:9]([C:8]([F:41])([F:7])[F:42])[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=1)[CH2:14][C:15]1[C:16]([N:25]([CH2:28][CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:26][CH3:27])=[N:17][C:18]2[CH2:19][CH2:20][CH2:21][CH2:22][C:23]=2[CH:24]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 58689747HCID 58689747, compound

Product 1

HCID 11592247HCID 11592247, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of potassium carbonate (0.269 g, 1.949 mmol) in dry THF (5 mL) was added a THF solution (10 mL) of {3-[(3,5-bis-trifluoromethyl-benzylamino)-methyl]-5,6,7,8-tetrahydro-quinolin-2-yl}-cyclopentylmethyl-ethylamine (0.25 g, 0.3 mmol), which was then stirred for 1 h. Methyl chloroformate (0.137 g, 1.46 mmol) was then added and stirring was was continued at RT for 8 h. The solvent was then evaporated, water was added, and the product was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was evaporated to afford a residue. This crude residue was purified over silica gel (100-200 mesh) and eluted with 2% ethyl acetate and petroleum ether to afford (3,5-bis-trifluoromethyl-benzyl)-[2-(cyclopentylmethyl-ethyl-amino)-5,6,7,8-tetrahydro-quinolin-3-ylmethyl]-carbamic acid methyl ester as light green, pasty compound (0.05 g), yield: 15%.

Workup

  1. stirringstirring
  2. waitwas was continued at RT for 8 h
  3. customThe solvent was then evaporated
  4. additionwater was added
  5. extractionthe product was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customthe solvent was evaporated
  8. customto afford a residue
  9. customThis crude residue was purified over silica gel (100-200 mesh)
  10. washeluted with 2% ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-6a886945952d4598b7fa84e74e76dbb8
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Reaction notes

Loading…