4-Chloroaniline → 2-(4-Bromo-phenyl)-N-(4-chloro-phenyl)-3-(diethylamino-pyrrolidin-1-yl)-propionamide

HRID 220193Notes

Reaction equation

HRID 220193 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][N:13]2[CH2:17][CH2:16][CH:15](N(CC)CC)[CH2:14]2)[C:9]([OH:11])=O)=[CH:4][CH:3]=1.CC[N:25]([CH:29]([CH3:31])C)[CH:26]([CH3:28])C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[Cl:56][C:57]1[CH:62]=[CH:61][C:60]([NH2:63])=[CH:59][CH:58]=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:12][N:13]2[CH2:14][CH2:15][CH2:16][CH:17]2[N:25]([CH2:26][CH3:28])[CH2:29][CH3:31])[C:9]([NH:63][C:60]2[CH:61]=[CH:62][C:57]([Cl:56])=[CH:58][CH:59]=2)=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 592382652-(4-Bromo-phenyl)-3-(3-diethylamino-pyrrolidin-1-yl)-propionic acid

Product 1

HCID 672315242-(4-Bromo-phenyl)-N-(4-chloro-phenyl)-3-(diethylamino-pyrrolidin-1-yl)-propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-bromo-phenyl)-3-(3-diethylamino-pyrrolidin-1-yl)-propionic acid (590 mg, 1.6 mmol), DIPEA (1.03 g, 8 mmol), and Pybrop (1.12 g, 2.4 mmol) in CH2Cl2 (10 mL) was added 4-chloro-phenylamine (306 mg, 2.4 mmol). This mixture was stirred overnight at room temperature and then evaporated. The mixture redissolved in EtOAc (20 mL) and washed with water, brine, dried with Na2SO4, concentrated in vacuo. The residue was purified by flash column chromatography to give a white solid. MS: calc'd 478 (MH+), exp 478 (MH+).

Workup

  1. customevaporated
  2. dissolutionThe mixture redissolved in EtOAc (20 mL)
  3. washwashed with water, brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography
  7. customto give a white solid

Sources & evidence

ORD record
ord-b9be3c2ad4224679ae5953d8dd11722f
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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