Triethylamine → 2-[(3-Chloro-4-fluoro-phenylamino)-(4-cyano-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 2204306Notes

Reaction equation

HRID 2204306 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].[CH2:10]([O:12][C:13]([C:15]1[CH:19]=[CH:18][N:17]([CH:20]([CH3:22])[CH3:21])[C:16]=1[CH:23](Cl)[C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=1)=[O:14])[CH3:11].CCN(CC)CC>CCOC(C)=O>[CH2:10]([O:12][C:13]([C:15]1[CH:19]=[CH:18][N:17]([CH:20]([CH3:22])[CH3:21])[C:16]=1[CH:23]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([F:9])=[C:2]([Cl:1])[CH:3]=1)[C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=1)=[O:14])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97083-Chloro-4-fluoroanilineHCID 867031102-[chloro-(4-cyano-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 867031092-[(3-Chloro-4-fluoro-phenylamino)-(4-cyano-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Chloro-4-fluoroaniline (6.40 mmol) was added at 0° C. to a solution of 2-[chloro-(4-cyano-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester (Step H3) (3.20 mmol). Then Et3N (9.60 mmol) was added and the mixture was stirred at rt for 1 h. The mixture was diluted with EtOAc. The organic layer was washed successively with H2O (2×), brine, dried (Na2SO4), filtered and concentrated. The product was purified by flash chromatography to afford the title compound. tR: 5.96 min (HPLC 4); ESI-MS: tR=1.35 min, [M+H]+ 440/442 (LC-MS 1).

Workup

  1. washThe organic layer was washed successively with H2O (2×), brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-4da33ad9c65f4ff19595aef6ba151478
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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