Diisopropylethylamine → 1-{[5-Bromo-4-(3-chloro-5-fluorophenyl)furan-2-yl]carbonyl}imidazolidin-4-one

HRID 2190132Notes

Reaction equation

HRID 2190132 reaction equation
BrC1C=C(C([N:16]2C[CH2:20][NH:19][C:18](=[O:22])[CH2:17]2)=O)OC=1C1C=CC=C(Cl)C=1.[Br:23][C:24]1[O:28][C:27]([C:29]([OH:31])=O)=[CH:26][C:25]=1[C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[C:34]([Cl:39])[CH:33]=1.C(N(CC)C(C)C)(C)C>>[Br:23][C:24]1[O:28][C:27]([C:29]([N:16]2[CH2:17][C:18](=[O:22])[NH:19][CH2:20]2)=[O:31])=[CH:26][C:25]=1[C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[C:34]([Cl:39])[CH:33]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 580647615-Bromo-4-(3-chloro-5-fluorophenyl)furan-2-carboxylic acidHCID 580647644-{[4-Bromo-5-(3-chlorophenyl)furan-2-yl]carbonyl}piperazin-2-one

Product 1

HCID 580647781-{[5-Bromo-4-(3-chloro-5-fluorophenyl)furan-2-yl]carbonyl}imidazolidin-4-one

Procedure

The preparation of the title compound takes place in analogy to the synthesis of the compound from Example 27A starting with the compound from Example 23A and the compound from Example 35A. 5 equivalents of N,N-diisopropylethylamine are used. The product is precipitated by the addition of water to the reaction solution. The precipitate is collected by suction filtration, washed with tetrahydrofuran and dried under high vacuum. 587 mg (97% of theory) of the title compound are obtained.

Workup

  1. customThe product is precipitated by the addition of water to the reaction solution
  2. filtrationThe precipitate is collected by suction filtration
  3. washwashed with tetrahydrofuran
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-c78b9f9c63f1415fb41298c3e447049b
Source dataset
uspto-grants-2012_12
Patent number
US08324268B2

Reaction notes

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