Acetic Acid → HCID 9865436, compound

HRID 365536Notes

Reaction equation

HRID 365536 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].C=O.[C:31]([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])[CH3:31])=[CH:9][CH:10]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 9951833HCID 9951833, compound2×

Product 1

HCID 9865436HCID 9865436, compoundYield 31%

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, 30 mg, 0.0788 mmol), formaldehyde (23.66 mg, 0.788 mmol), sodium cyanoborohydride (3.9 mg, 0.788 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 (5% ethyl acetate in hexane, Rf=0.27) to give the title compound(9.5 mg, 31%) as a white solid:

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by silica gel chromatography (5% ethyl acetate in hexane, Rf=0.27)

Sources & evidence

ORD record
ord-28b75a3528134534ab41c76fd3ec3210
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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