Hydrochloric Acid → HCID 66703837, compound

HRID 426019Notes

Reaction equation

HRID 426019 reaction equation
[CH:1]1([NH:7][C:8]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:9]=2[C:10]([NH:12][C:13]2[CH:22]=[C:21]3[C:16]([CH2:17][CH2:18][C:19](=[O:27])[N:20]3[CH2:23][C:24](O)=[O:25])=[CH:15][CH:14]=2)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:36][NH2:37].C1COCC1.Cl>CO>[CH:1]1([NH:7][C:8]2[CH:31]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:29]=[CH:28][C:9]=2[C:10]([NH:12][C:13]2[CH:22]=[C:21]3[C:16]([CH2:17][CH2:18][C:19](=[O:27])[N:20]3[CH2:23][C:24]([NH:37][CH3:36])=[O:25])=[CH:15][CH:14]=2)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 8028TetrahydrofuranHCID 66703843HCID 66703843, compound

Product 1

HCID 66703837HCID 66703837, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [7-{[2-(cyclohexylamino)-4-(trifluoromethyl)benzoyl]amino}-2-oxo-3,4-dihydroquinolin-1(2H)-yl]acetic acid (70 mg), N,N′-carbonyldiimidazole (70 mg), methylamine aqueous solution (1 mL) and THF was stirred at room temperature for 3 hours, mixed with methanol and stirred for 20 minutes. A 0.5 M hydrochloric acid was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol, 20:1 to 10:1) to obtain 2-(cyclohexylamino)-N-{1-[2-(methylamino)-2-oxoethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl}-4-(trifluoromethyl)benzamide (12 mg) as a solid.

Workup

  1. stirringstirred for 20 minutes
  2. extractionfollowed by extraction with ethyl acetate
  3. concentrationThe organic layer was concentrated under a reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform:methanol, 20:1 to 10:1)

Sources & evidence

ORD record
ord-5a75504407e843639ce1ccdaf4c45d76
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

Loading…