Diisopropylethylamine → 2-Bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-ethyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

HRID 2204310Notes

Reaction equation

HRID 2204310 reaction equation
[Br:1][C:2]1[N:6]([CH2:7][CH3:8])[C:5]([CH:9]([NH:17][C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[CH3:25])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[C:4]([C:26](O)=[O:27])[CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>O>[Br:1][C:2]1[N:6]([CH2:7][CH3:8])[C:5]2[CH:9]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)[N:17]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=3[CH3:25])[C:26](=[O:27])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 867031155-bromo-2-[(5-chloro-2-methyl-phenylamino)-(4-chloro-phenyl)-methyl]-1-ethyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 867031142-Bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-ethyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5-bromo-2-[(5-chloro-2-methyl-phenylamino)-(4-chloro-phenyl)-methyl]-1-ethyl-1H-pyrrole-3-carboxylic acid (Step K1) (3.11 mmol), TBTU (4.36 mmol) and DIEA (9.33 mmol) was stirred at 80° C. for 1 h. The reaction mixture was diluted with H2O and extracted with EtOAc (2×). The combined organic layers were washed successively with H2O and brine, dried (MgSO4), filtered and concentrated. The product was purified by chromatography column to afford the title compound as a colorless oil. tR: 5.90 min (HPLC 4); ESI-MS: tR=1.35 min, [M+H]+ not ionized (LC-MS 1).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed successively with H2O and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by chromatography column

Sources & evidence

ORD record
ord-b6c5cb40b4904a68bfb17da43280dfd8
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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