Acetic Acid → Ethyl 4-[(1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)(cyclopropylmethyl)amino]benzoate

HRID 365529Notes

Reaction equation

HRID 365529 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([O-:21])=[O:20])=[CH:17][CH:16]=3)[CH:12]=2)[C:7]([CH3:25])([CH3:24])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH2:26]1[CH:28]([CH:29](O)C#N)[CH2:27]1.C([BH3-])#N.[Na+].[C:37](O)(=O)[CH3:38]>C(#N)C>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N:14]([CH2:29][CH:28]3[CH2:27][CH2:26]3)[C:15]3[CH:16]=[CH:17][C:18]([C:19]([O:21][CH2:37][CH3:38])=[O:20])=[CH:22][CH:23]=3)[CH:12]=2)[C:7]([CH3:25])([CH3:24])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 113893592-Cyclopropyl-2-hydroxyacetonitrileHCID 232919314-[(1-Isopropyl-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-7-yl)amino]benzoate2×

Product 1

HCID 9866826Ethyl 4-[(1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)(cyclopropylmethyl)amino]benzoateYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-[(1-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydroquinolin-7-yl)amino]benzoate (Compound 34, 9.4 mg, 0.0256 mmol), cyclopropylcarboxaldehyde (8.99 mg, 0.1282 mmol), sodium cyanoborohydride (8.06 mg, 0.1282 mmol), acetic acid (0.125 mL), and acetonitrile (1 mL) was stirred at room temperature for 3 days. The solvent was removed and the residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.48) to give the title compound (8.03 mg, 75%) as a solid: PNMR (300 MHz, CDCl3): δ0.19 (m, 2 H), 0.49 (m, 2 H), 1.16 (d, 6 H, J=6.5 Hz), 1.30 (s, 6 H), 1.35 (t, 3 H, J=7.1 Hz), 1.73 (t, 2 H, J=6.0 Hz), 3.17 (t, 2 H, J=6.0 Hz), 3.56 (d, 2 H, J=6.5 Hz), 3.99 (sp, 1 H, J=6.6 Hz), 4.31 (q, 2 H, J=7.1 Hz), 6.43 (dd, 1 H, J=8.1, 2.0 Hz), 6.53 (d, 1 H, J=3.6 Hz), 7.71 (d, 2 H, J=9.0 Hz), 7.18 (d, 1 H, J=8.0 Hz), 7.83 (d, 2 H, J=9.0 Hz).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.48)

Sources & evidence

ORD record
ord-8911c8db564f4a65adaf14f8b99663bb
Source dataset
uspto-grants-2000_10
Patent number
US06127382

Reaction notes

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