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Triethylamine → 4-Chloro-N-[5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2,2-dimethylpropanoyl)furo[2,3-b]pyridin-3-yl]butanamide

HRID 8798
Notes
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Reaction equation

HRID 8798 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[CH:9]=2)[O:4][C:3]=1[C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].[Cl:32][CH2:33][CH2:34][CH2:35][C:36](Cl)=[O:37].C(N(CC)CC)C>C(Cl)Cl>[Cl:32][CH2:33][CH2:34][CH2:35][C:36]([NH:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[CH:9]=2)[O:4][C:3]=1[C:26](=[O:31])[C:27]([CH3:28])([CH3:30])[CH3:29])=[O:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 102542841-(3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl)-2,2-dimethylpropan-1-one

Product 1

HCID 100996934-Chloro-N-[5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2,2-dimethylpropanoyl)furo[2,3-b]pyridin-3-yl]butanamide

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a magnetically stirred solution of 0.300 g (0.63 mmol) of the product of Example 17 in 6 mL of CH2Cl2 at 0° C. was added 70 μL (0.63 mmol) of 4-chlorobutyryl chloride and 96 mg (0.95 mmol) of triethylamine. The reaction was stirred for 1.5 h and allowed to warm to room temperature. The reaction mixture was then partitioned between saturated aqueous NaHCO3 and EtOAc. The organic layer was separated, washed with aq. NaHCO3, brine, then dried (Na2SO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0–20% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound. HPLC/MS: 577.0 (M+1), 578.9 (M+3); Rt=5.05 min.

Workup

  1. customThe reaction mixture was then partitioned between saturated aqueous NaHCO3 and EtOAc
  2. customThe organic layer was separated
  3. washwashed with aq. NaHCO3, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on a silica gel flash chromatography column
  8. washeluted with 0–20% EtOAc-hexane
  9. customEvaporation of the purified fractions
  10. customdrying in vacuo

Sources & evidence

ORD record
ord-f47096e8f5d1498496da5e56b2bf7d62
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091216B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes