Water → HCID 66624968, compound

HRID 2167277Notes

Reaction equation

HRID 2167277 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([NH2:16])=[O:15])=[CH:11][CH:12]=2)[C@H: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][C@@H:5]1[CH3:30])(=[O:3])[CH3:2].[CH:31](N(CC)C(C)C)(C)C.CCl.N[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([OH:50])=[O:49].O>ClCCl>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([NH:16][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([O:50][CH3:31])=[O:49])=[O:15])=[CH:11][CH:12]=2)[C@H: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][C@@H:5]1[CH3:30])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 66625546HCID 66625546, compoundHCID 86660762HCID 86660762, compound

Product 1

HCID 66624968HCID 66624968, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

81.9 mg of (2S,4R)-1-acetyl-2-methyl-4-[(4-morpholinophenyl)amino]-1,2,3,4-tetrahydroquinoline-6-carboxamide was dissolved in 2 mL of dichloromethane, and 174.2 μL of N,N-diisopropylethylamine and 124.9 mg of hexafluorophosphate(benzotriazol-1-yloxy)tripyrrolidinophos phonium were added to the solution. The mixture was stirred for one hour at room temperature. Subsequently, 108.9 mg of 6-aminohexanoate methyl-monohydrochloride was added thereto, and the mixture was stirred for one hour at room temperature. After completion of the reaction, water was added to the reaction mixture, and then 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 thus 54.0 mg (50.3%, cis-form only) of the title compound was obtained as a pale yellow crystalline powder.

Workup

  1. stirringthe mixture was stirred for one hour 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 obtained as a pale yellow crystalline powder

Sources & evidence

ORD record
ord-d13dc1de966d4ce9b4a43bfb970b9768
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

Loading…