p-Toluenesulfonic acid → HCID 178439042, compound

HRID 629852Notes

Reaction equation

HRID 629852 reaction equation
[CH:1]1([NH:7][CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[C:19]2[N:24]=[C:23]([CH:25]=O)[CH:22]=[CH:21][CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:27]([C:30]1[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]([CH3:39])[CH3:38])[C:31]=1[NH2:32])([CH3:29])[CH3:28].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH:1]1([NH:7][CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[C:19]2[N:24]=[C:23](/[CH:25]=[N:32]/[C:31]3[C:33]([CH:37]([CH3:38])[CH3:39])=[CH:34][CH:35]=[CH:36][C:30]=3[CH:27]([CH3:29])[CH3:28])[CH:22]=[CH:21][CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 32484DiisopropylanilineHCID 118340992HCID 118340992, compound

Product 1

HCID 178439042HCID 178439042, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 9.80 g (28.0 mmol) of 6-{2-[(cyclohexylamino)methyl]-1-naphthyl}pyridine-2-carbaldehyde, 5.55 g (31.0 mmol) of 2,6-diisopropylaniline, 0.1 g of TsOH in 100 ml of dry ethanol was refluxed for 10 h in argon atmosphere. The resulting mixture was cooled to room temperature and then evaporated to dryness. The residue was purified by flash chromatography on silica gel 60 (40-63 um, eluent: hexane-ethyl acetate-triethylamine=10:1:1, vol.). Yield 10.8 g (77%) of yellow powder. Anal. Calc for C35H41N3: C 83.45; H 8.20; N 8.34. Found: C 83.59; H 8.06; N 8.41.1H NMR (CDCl3): δ 8.39 (m, 1H, 3-H in Py), 8.35 (s, 1H, CHN), 8.00 (m, 1H, 4-H in Py), 7.87-7.92 (m, 2H, 4,8-H in naphthyl), 7.63 (m, 1H, 3-H in naphthyl), 7.54 (m, 1H, 3-H in Py), 7.37-7.47 (m, 3H, 5-H in Py and 6,7-H in naphthyl), 7.09-7.17 (m, 3H, 3,4,5-H in naphthyl), 3.69 (m, 2H, CH2N), 3.01 (sept, J=6.8 Hz, 2H, CH in 2,6-diisopropylphenyl), 2.29 (m, 1H, CH in Cy), 1.61-1.72 (m, 4H, Cy), 1.52-1.54 (m, 2H, Cy), 1.19 (d, J=6.8 Hz, 12H, CH3 in 2,6-diisopropylphenyl), 1.09-1.11 (m, 2H, Cy), 0.94-0.99 (m, 2H, Cy).

Workup

  1. customevaporated to dryness
  2. customThe residue was purified by flash chromatography on silica gel 60 (40-63 um, eluent: hexane-ethyl acetate-triethylamine=10:1:1, vol.)

Sources & evidence

ORD record
ord-87e2139efb864380975cbb2b69217d36
Source dataset
uspto-grants-2016_04
Patent number
US09315526B2

Reaction notes

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