Acetic Acid → HCID 9888509, compound

HRID 365538Notes

Reaction equation

HRID 365538 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16]([CH3:26])([CH3:25])[CH2:17][CH2:18][N:19]3[CH:22]([CH3:24])[CH3:23])=[CH:14][C:13]=2[CH3:27])=[CH:7][CH:6]=1)[CH3:2].[CH:29](=O)[CH2:30][CH3:31].C([BH3-])#N.[Na+].C(O)(=O)C>C(#N)C>[CH2:1]([O:3][C:4](=[O:28])[C:5]1[CH:6]=[CH:7][C:8]([N:11]([C:12]2[CH:21]=[C:20]3[C:15]([C:16]([CH3:25])([CH3:26])[CH2:17][CH2:18][N:19]3[CH:22]([CH3:23])[CH3:24])=[CH:14][C:13]=2[CH3:27])[CH2:29][CH2:30][CH3:31])=[CH:9][CH:10]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 9951833HCID 9951833, compound2×

Product 1

HCID 9888509HCID 9888509, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(1-isopropyl-4,4,6-trimethyl-1,2,3,4-tetrahydroquinolin-7-ylamino)-benzoic acid ethyl ester (Compound 46, 60.3 mg, 0.1585 mmol), propionaldehyde (36.4 mg, 0.792 mmol), sodium cyanoborohydride (49.77 mg, 0.792 mmol), acetic acid (0.125 mL), and acetonitrile (1 mL) was stirred at room temperature overnight. The solvent was removed and the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.44) to give the title compound (12.0 mg, 18%) as a solid:

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.44)

Sources & evidence

ORD record
ord-7703f6c0bbed4140824671dba4900b7c
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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