1-Chloro-N,N-2-trimethylpropenylamine → 2-[chloro-(4-cyano-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 2204307Notes

Reaction equation

HRID 2204307 reaction equation
[Cl:1]C(N(C)C)=C(C)C.[CH2:9]([O:11][C:12]([C:14]1[CH:18]=[CH:17][N:16]([CH:19]([CH3:21])[CH3:20])[C:15]=1[CH:22]([C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=1)O)=[O:13])[CH3:10]>C(Cl)Cl>[CH2:9]([O:11][C:12]([C:14]1[CH:18]=[CH:17][N:16]([CH:19]([CH3:21])[CH3:20])[C:15]=1[CH:22]([Cl:1])[C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=1)=[O:13])[CH3:10]

Participants

4

Reactant 2

HCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 867031112-[(4-cyano-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Chloro-N,N,2-trimethylpropenylamine [26189-59-3] (4.80 mmol) was added to a solution of 2-[(4-cyano-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester (Step H4) (3.20 mmol) in CH2Cl2 (15 mL) and the mixture was stirred at rt for 2.5 h. CH2Cl2 was added and the reaction mixture was concentrated to dryness (2×) to afford the title compound as a yellow-orange oil. tR: 5.71 min (sample in MeOH) (HPLC 4); ESI-MS: tR=1.26 min (LC-MS 1).

Workup

  1. concentrationthe reaction mixture was concentrated to dryness (2×)

Sources & evidence

ORD record
ord-8906da3d00bf4f29801e301008aa88e6
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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