Hydrochloric Acid → HCID 58032150, compound

HRID 2167268Notes

Reaction equation

HRID 2167268 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([OH:16])=O)=[CH:11][CH:12]=2)[C@H:7]([O:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[CH2:6][C@@H:5]1[CH3:30])(=[O:3])[CH3:2].Cl.C1C=CC2N(O)N=[N:38][C:36]=2C=1.CN>ClCCl.O>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([NH:38][CH3:36])=[O:16])=[CH:11][CH:12]=2)[CH:7]([O:17][C:18]2[CH:19]=[CH:20][C:21]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:22][CH:23]=2)[CH2:6][CH:5]1[CH3:30])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 66625756HCID 66625756, compound

Product 1

HCID 58032150HCID 58032150, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

48.6 mg of (2S,4R)-1-acetyl-2-methyl-4-(4-morpholinophenoxy)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid, 27.2 mg of WSCD.HCl, and 24.6 mg of HOBt.H2O were dissolved in 1 mL of dichloromethane, and the solution was stirred for 1.5 hours at room temperature. 178 μL of monomethylamine (2.0 M tetrahydrofuran solution) was added to the reaction liquid, and the mixture was stirred for another 1.5 hours at room temperature. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted three times with chloroform. The extraction product was washed with saturated brine, dehydrated over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (chloroform:methanol=10:1), and then was recrystallized from chloroform-hexane. Thus, 27.2 mg (53.3%, cis:trans=15:1) of the title compound was obtained as a white crystalline powder.

Workup

  1. stirringthe mixture was stirred for another 1.5 hours at room temperature
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was extracted three times with chloroform
  4. washThe extraction product was washed with saturated brine
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified
  7. customwas recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-364d2844cce4456d9076c7d69b4b787d
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

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