Water → N-{6-[2-(4-benzo[1,3]dioxol-5-ylmethylpiperazine-1-carbonyl)-1H-indol-5-yloxy]pyridin-3-yl}-3,4-dichlorobenzamide

HRID 1038772Notes

Reaction equation

HRID 1038772 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19]([C:24]([OH:26])=O)=[CH:18]3)=[N:12][CH:13]=1)=[O:6].[O:31]1[C:35]2[CH:36]=[CH:37][C:38]([CH2:40][N:41]3[CH2:46][CH2:45]C[CH2:43][CH2:42]3)=[CH:39][C:34]=2[O:33][CH2:32]1.Cl.C([N:50]=C=NCCCN(C)C)C.O>C1COCC1>[O:31]1[C:35]2[CH:36]=[CH:37][C:38]([CH2:40][N:41]3[CH2:42][CH2:43][N:50]([C:24]([C:19]4[NH:20][C:21]5[C:17]([CH:18]=4)=[CH:16][C:15]([O:14][C:11]4[N:12]=[CH:13][C:8]([NH:7][C:5](=[O:6])[C:4]6[CH:27]=[CH:28][C:29]([Cl:30])=[C:2]([Cl:1])[CH:3]=6)=[CH:9][CH:10]=4)=[CH:23][CH:22]=5)=[O:26])[CH2:45][CH2:46]3)=[CH:39][C:34]=2[O:33][CH2:32]1

Participants

6

Reactant 4

HCID 962WaterHCID 7831081-(1,3-Benzodioxol-5-ylmethyl)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 684941705-[5-(3,4-dichlorobenzoylamino)pyridin-2-yloxy]-1H-indole-2-carboxylic acid

Product 1

HCID 68497901N-{6-[2-(4-benzo[1,3]dioxol-5-ylmethylpiperazine-1-carbonyl)-1H-indol-5-yloxy]pyridin-3-yl}-3,4-dichlorobenzamideYield 98.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-[5-(3,4-Dichlorobenzoylamino)pyridin-2-yloxy]-1H-indole-2-carboxylic acid (0.250 g, 0.565 mmol) was dissolved in THF (20 mL). To the solution were added 1-benzo[1,3]dioxol-5-ylmethylpiperadine (0.125 g, 0.565 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.119 g, 0.622 mmol), and the resulting solution was stirred for 15 hours at room temperature. Water (50 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (40 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=30:1) to yield 0.360 g of the title compound as a pale yellow powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (40 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=30:1)

Sources & evidence

ORD record
ord-d0e581e3fc7f4a7b87de6fd6be868c5e
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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