Hydrochloric Acid → HCID 58032165, compound

HRID 2167260Notes

Reaction equation

HRID 2167260 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14](O)=[O:15])=[CH:11][CH:12]=2)[CH:7]([NH: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][CH:5]1[CH3:30])(=[O:3])[CH3:2].Cl.C1C=CC2N(O)[N:39]=[N:38]C=2C=1.O.NN.C(=O)([O-])O.[Na+]>ClCCl.O>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([NH:38][NH2:39])=[O:15])=[CH:11][CH:12]=2)[CH:7]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)=[CH:20][CH:19]=2)[CH2:6][CH:5]1[CH3:30])(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 66625463HCID 66625463, compound

Product 1

HCID 58032165HCID 58032165, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

[Step 4] 102 mg of 1-acetyl-4-[(4-morpholinophenyl)amino]-2-methyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid, 125 mg of WSCD.HCl, and 72 mg of HOBt.H2O were dissolved in 1 mL of dichloromethane, and 0.12 mL of hydrazine monohydrate was added to the solution. The mixture was stirred overnight at room temperature. After completion of the reaction, a saturated aqueous solution of sodium hydrogen carbonate was added to the 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 (methanol:chloroform=1:10), and thus 83 mg (cis:trans=3:1, 79) of the title compound was obtained as a brown oily substance.

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted three times with chloroform
  3. washThe extraction product was washed with saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified
  6. customwas obtained as a brown oily substance

Sources & evidence

ORD record
ord-c929fce561de4ffea4fc484d75f390b3
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

Loading…