Piperidine → HCID 57901625, compound

HRID 1851462Notes

Reaction equation

HRID 1851462 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([OH:20])=O)=[CH:14]2)=[O:7].[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(OCC)(=O)C.CN(C)C=O>[N:21]1([C:18]([C:15]2[NH:16][C:17]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[O:7])=[O:20])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57901652HCID 57901652, compound

Product 1

HCID 57901625HCID 57901625, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 7-[(2-thienylcarbonyl)amino]-1H-indole-2-carboxylic acid (100 mg), piperidine (42 μL), 1H-1,2,3-benzotriazol-1-ol (75 mg) and N,N-dimethylformamide (4 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (94 mg) at 4° C., and the mixture was stirred at room temperature for 2 days. The reaction mixture was diluted with ethyl acetate, washed with aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:9-6:4) and the obtained oil was recrystallized from diethyl ether to give the title compound (115 mg, yield 93%) as colorless prism crystals. melting point 131-132° C.

Workup

  1. washwashed with aqueous sodium hydrogencarbonate solution, water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe obtained oil was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-58d49f820e8e4e2092ac703f26fb9e2c
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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