1-Hydroxybenzotriazole → HCID 58306720, compound

HRID 1909852Notes

Reaction equation

HRID 1909852 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17](O)=[O:18])[CH2:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.Cl.[NH2:23][C@H:24]([C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1)[CH3:25].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>O.CN(C=O)C.N1C=CC=CC=1>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]([NH:23][C@H:24]([C:26]3[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=3)[CH3:25])=[O:18])[CH2:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57462942(S)-Methyl 4-(1-aminoethyl)benzoate hydrochlorideHCID 58307054HCID 58307054, compound

Product 1

HCID 58306720HCID 58306720, compoundYield 27.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(4-chlorobenzyl)-1,2,3,4-tetrahydroquinoline-8-carboxylic acid (310 mg), methyl 4-[(1S)-1-aminoethyl]benzoate hydrochloride (240 mg), EDCI.HCl (210 mg), HOBt (160 mg), pyridine (0.25 mL), and DMF (3.00 mL) was stirred at room temperature for 3 days. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain methyl 4-[(1S)-1-({[1-(4-chlorobenzyl)-1,2,3,4-tetrahydroquinolin-8-yl]carbonyl}amino)ethyl]benzoate (129 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-e5e506bd28b649f1ac53dcfbdf8ed991
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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