Triethylamine → HCID 71233967, compound

HRID 710028Notes

Reaction equation

HRID 710028 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH2:20][CH2:19]1)[C:12](O)=[O:13])=[O:7].C(N(CC)CC)C.[C:38]1([CH2:44][CH2:45][CH2:46][NH2:47])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)Cl>[C:38]1([CH2:44][CH2:45][CH2:46][NH:47][C:12]([C:11]2[CH:15]=[CH:16][C:17]([N:18]3[CH2:23][CH2:22][N:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH3:30])[CH2:20][CH2:19]3)=[C:9]([NH:8][C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[O:7])[CH:10]=2)=[O:13])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 162593-PhenylpropylamineHCID 71224789HCID 71224789, compound

Product 1

HCID 71233967HCID 71233967, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-[(furan-2-carbonyl)-amino]-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid (0.1 g, 0.246 mmol) in methylene dichloride (5 ml), triethylamine (0.074 g, 0.74 mmol), (3-phenylpropyl)amine (0.044 g, 0.370 mmol) and 1-propane phosphonic cyclic anhydride (0.23 g, 0.74 mmol) were added. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated and extracted with dichloromethane (10 ml×1). The organic layer was washed with water (10 ml×2) and dried over anhydrous sodium sulfate. The organic layer was concentrated and the crude product obtained was purified by flash chromatography using silica gel column to get (0.070 g, 67.9%) of the titled compound as a brown solid.

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with dichloromethane (10 ml×1)
  4. washThe organic layer was washed with water (10 ml×2)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe organic layer was concentrated
  7. customthe crude product obtained
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-f39b189caedb407a89fd1b4e7b6720e1
Source dataset
uspto-grants-2015_11
Patent number
US09181226B2

Reaction notes

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