Triethylamine → HCID 67327734, compound

HRID 1158653Notes

Reaction equation

HRID 1158653 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][NH:12][CH2:11][CH:10]2[CH:14]([O:16][C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][N:18]=2)[CH3:15])[CH:5]=[CH:6][C:7]=1[Cl:8].CCN(CC)CC.[Br:32][CH2:33][C:34](Cl)=[O:35]>C(Cl)Cl>[Br:32][CH2:33][C:34]([N:12]1[CH2:13][CH:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH:10]([CH:14]([O:16][C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][N:18]=2)[CH3:15])[CH2:11]1)=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 89602Bromoacetyl chlorideHCID 669997186-{(SR)-1-[(3RS,4SR)-4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile

Product 1

HCID 67327734HCID 67327734, compoundYield 703.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-{(SR)-1-[(3RS,4SR)-4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile (XV-B-4) 30 mg (0.083 mmol) in CH2Cl2 (3 mL) at RT, 0.013 ml (0.01 mmol) of Et3N and 0.0083 mL (0.01 mmol) of bromo-acetyl chloride were added. Stirring was continued over night and then concentrated under vacuo. The crude residue was dissolved in EtOAc, washed with H2O. The organic phase was dried over Na2SO4 and the product was purified by flash chromatography (SiO2, EtOAc) to yield the title product 34 mg (85%) as a colorless oil.

Workup

  1. waitwas continued over night
  2. concentrationconcentrated under vacuo
  3. dissolutionThe crude residue was dissolved in EtOAc
  4. washwashed with H2O
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customthe product was purified by flash chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-2777440fad8a498186d21e5179f3065c
Source dataset
uspto-grants-2010_10
Patent number
US07812021B2

Reaction notes

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