Proton sponge → HCID 69416303, compound

HRID 1296354Notes

Reaction equation

HRID 1296354 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[C:18]([CH3:19])=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[N:16]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:33])[N:15]=2)[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O.CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1>ClCCCl>[ClH:26].[Cl:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[N:16]1[C:17]([C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)=[C:18]([CH3:19])[C:14]([CH:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[N:15]1

Participants

5

Reactant 3

HCID 88675Proton spongeHCID 5213051-Chloroethyl chloroformateHCID 69417374HCID 69417374, compound

Product 1

HCID 69416303HCID 69416303, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The solution of 4-benzyl-2-[5-(4-chlorophenyl)-1-(2-chlorophenyl)-4-methyl-1H-pyrazol-3-yl]-morpholine 5A-1 (840 mg, 1.7 mmol), 1-chloroethyl chloroformate (0.2 ml, 1.87 mmol), and 1,8-bis(dimethylamino)naphthalene (72 mg, 0.34 mmol) in 5 ml 1,2-dichloroethane was heated to 50° C. for 3 hours. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was dissolved in 5 ml MeOH and heated to reflux for 2 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and concentrated. The residue was stirred in 5 ml diethyl ether and the product was precipitated and collected by filtration to give the title compound 5A-2 as a white solid (525 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in 5 ml MeOH
  3. temperatureheated
  4. temperatureto reflux for 2 hours
  5. temperaturethe reaction mixture was cooled to room temperature
  6. concentrationconcentrated
  7. customthe product was precipitated
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-cfc0dfd50c8a4eb7b0eb6824f393f1e5
Source dataset
uspto-grants-2007_07
Patent number
US07247628B2

Reaction notes

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