Hydrochloric Acid → HCID 58032176, compound

HRID 2167259Notes

Reaction equation

HRID 2167259 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)[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=[N:38][C:36]=2C=1.CN.O1CCCC1.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][CH3:36])=[O:16])=[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 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 66615946Methylamine tetrahydrofuranHCID 66625463HCID 66625463, compound

Product 1

HCID 58032176HCID 58032176, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

72 mg of 1-acetyl-4-[(4-morpholinophenyl)amino]-2-methyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid (compound of Step 3 of Example 111), 51 mg of WSCD.HCl, and 36 mg of HOBt.H2O were dissolved in 2 mL of dichloromethane, and 0.4 mL of a 2 M methylamine/tetrahydrofuran solution was added to the solution. The resulting 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 52 mg (cis:trans=4:1, 70%) of the title compound was obtained as a yellow solid.

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 yellow solid

Sources & evidence

ORD record
ord-f61a2f5b89464beb8b72dfd36728d22c
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

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