Hydrochloric Acid → HCID 86732514, compound

HRID 2167262Notes

Reaction equation

HRID 2167262 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=NC=2C=1.O.Cl.[CH3:44][O:45][NH2:46].C(=O)([O-])O.[Na+]>ClCCl.C(N(CC)CC)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([NH:46][O:45][CH3:44])=[O:16])=[CH:11][CH:12]=2)[CH:7]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)=[CH:22][CH:23]=2)[CH2:6][CH:5]1[CH3:30])(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66625463HCID 66625463, compound

Product 1

HCID 86732514HCID 86732514, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

74 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), 52 mg of WSCD.HCl, 37 mg of HOBt-H2O, and 45 mg of methoxyamine hydrochloride were dissolved in 2 mL of dichloromethane, and 76 μL of triethylamine 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 57 mg (cis:trans=4:1, 72%) 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-ab02293b064d49e48d6aef7b88e52aea
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

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