Sulfuric Acid → HCID 11583821, compound

HRID 1785964Notes

Reaction equation

HRID 1785964 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[CH:14]([CH3:32])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.CO[CH:35]1[CH2:39][CH2:38][CH:37](OC)O1.OS(O)(=O)=O.NC1C=CC=CC=1.C([O-])(O)=O.[Na+]>CO.C1COCC1>[CH3:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([C:22]([N:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@H:12]([N:8]([C:5]3[CH:6]=[CH:7][C:2]([N:1]4[CH:35]=[CH:39][CH:38]=[CH:37]4)=[CH:3][CH:4]=3)[C:9](=[O:11])[CH3:10])[CH2:13][C@@H:14]2[CH3:32])=[O:31])=[CH:28][CH:27]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 6115AnilineHCID 790982,5-DimethoxytetrahydrofuranHCID 516892Sodium BicarbonateHCID 68922200HCID 68922200, compound

Product 1

HCID 11583821HCID 11583821, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

N-(4-amino-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (22 mg, 0.05 mmol) was dissolved in MeOH:THF (1 mL each) and cooled to 10° C. 2,5-dimethoxy-tetrahydrofuran (1.25 equiv.) was dissolved in THF and catalytic H2SO4, and added drop wise to the aniline mixture. The mixture was poured into sat. NaHCO3 and extracted with ethyl acetate. The organic layer was dried, filtered and concentrated, and the crude residue was purified by preparative HPLC to afford the title compound as an off-white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-488ed7ba3be84fecb01dc4ac52382e51
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

Loading…