1-Hydroxybenzotriazole → HCID 58913034, compound

HRID 1297023Notes

Reaction equation

HRID 1297023 reaction equation
[C:1]1([CH:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:8][CH2:9][O:10][C:11]([C:13]2[CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21](Cl)[CH:20]=3)[C:17]([C:26]([O-])=[O:27])=[C:16]([CH3:29])[NH:15][C:14]=2[CH3:30])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:37].CN(C)CCCN=C=NCC.O[N:50]1[C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][C:53]=2N=N1>ClCCl>[C:1]1([CH:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:8][CH2:9][O:10][C:11]([C:13]2[CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:37])[CH:20]=3)[C:17]([C:26]([N:50]3[CH2:55][CH2:56][CH2:57][CH2:58][CH2:53][CH2:54]3)=[O:27])=[C:16]([CH3:29])[NH:15][C:14]=2[CH3:30])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86586136HCID 86586136, compound

Product 1

HCID 58913034HCID 58913034, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

152 mg (0.303 mmol) of mono(3,3-diphenylpropane-1-yl)4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 45.0 mg (0.454 mmol) of hexamethyleneimine were dissolved in 20 ml of dichloromethane. 87.1 mg (0.454 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 46.4 mg (0.303 mmol) of 1-hydroxybenzotriazole were added to the obtained solution, and they were stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and then washed with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to obtain the title compound.

Workup

  1. washwashed with saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by the silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1)

Sources & evidence

ORD record
ord-2c2ab26df03f4873bec8679654f8fed5
Source dataset
uspto-grants-2007_07
Patent number
US07247645B2

Reaction notes

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