Triethylamine → HCID 42602840, compound

HRID 1038769Notes

Reaction equation

HRID 1038769 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH2:18][C:19]([N:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]4[CH:36]=[CH:35][C:31]5[O:32][CH2:33][O:34][C:30]=5[CH:29]=4)[CH2:23][CH2:22]2)=[O:20])[CH2:13][CH2:12]3)=[N:6][CH:7]=1.C(N(CC)CC)C.[Cl:44][C:45]1[CH:46]=[C:47]([CH:51]=[CH:52][C:53]=1[Cl:54])[C:48](Cl)=[O:49]>C1COCC1.[Cl-].[Na+].O>[O:32]1[C:31]2[CH:35]=[CH:36][C:28]([CH2:27][N:24]3[CH2:23][CH2:22][N:21]([C:19](=[O:20])[CH2:18][N:14]4[C:15]5[C:11](=[CH:10][C:9]([O:8][C:5]6[N:6]=[CH:7][C:2]([NH:1][C:48](=[O:49])[C:47]7[CH:51]=[CH:52][C:53]([Cl:54])=[C:45]([Cl:44])[CH:46]=7)=[CH:3][CH:4]=6)=[CH:17][CH:16]=5)[CH2:12][CH2:13]4)[CH2:26][CH2:25]3)=[CH:29][C:30]=2[O:34][CH2:33]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 68496888HCID 68496888, compound

Product 1

HCID 42602840HCID 42602840, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-[5-(5-Aminopyridin-2-yloxy)-2,3-dihydroindol-1-yl]-1-(4-benzo[1,3]dioxol-5-ylmethylpiperazin-1-yl)ethanone (0.240 g, 0.492 mmol) was dissolved in THF (10 mL). To the solution were added triethylamine (0.0686 mL, 0.492 mmol), then 3,4-dichlorobenzoyl chloride (0.103 g, 0.492 mmol), and the resulting solution was stirred for 30 minutes at room temperature. Brine (50 ml) was added to the reaction solution, and the mixture was extracted with ethyl acetate (50 mL). After the organic layer was washed with brine, then dried over anhydrous sodium sulfate, the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (CH2Cl2:MeOH=40:1), to yield 0.143 g of the title compound as a grayish white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (50 mL)
  2. washAfter the organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customThe obtained residue was purified by silica gel column chromatography (CH2Cl2:MeOH=40:1)

Sources & evidence

ORD record
ord-49150ba88fe54301bcf5e1199f1ef389
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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