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

HRID 2190130Notes

Reaction equation

HRID 2190130 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:14]([N:16]2[CH2:21]C[NH:19][C:18](=[O:22])[CH2:17]2)=[O:15])[O:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1.BrC1C=C(C(O)=O)OC=1C1C=CC=C(Cl)C=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>>[Br:1][C:2]1[CH:3]=[C:4]([C:14]([N:16]2[CH2:17][C:18](=[O:22])[NH:19][CH2:21]2)=[O:15])[O:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 580647644-{[4-Bromo-5-(3-chlorophenyl)furan-2-yl]carbonyl}piperazin-2-oneHCID 580647974-Bromo-5-(3-chlorophenyl)furan-2-carboxylic acid

Product 1

HCID 580647831-{[4-Bromo-5-(3-chlorophenyl)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 24A and the compound from Example 35A. 1.1 equivalents of PyBOP and 2.5 equivalents of N,N-diisopropylethylamine are used. During the reaction, the product precipitates. The precipitate is collected by suction filtration, washed with tetrahydrofuran and dried under high vacuum. 870 mg (71% of theory) of the title compound are obtained.

Workup

  1. customDuring the reaction
  2. customthe product precipitates
  3. filtrationThe precipitate is collected by suction filtration
  4. washwashed with tetrahydrofuran
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-face59e24ca947948473f00ce2f18566
Source dataset
uspto-grants-2012_12
Patent number
US08324268B2

Reaction notes

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