p-Toluenesulfonic acid monohydrate → 2-(4,5-Dimethoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl) aminomethylbenzoxazole

HRID 2213982Notes

Reaction equation

HRID 2213982 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[C:14]=3[N:15]=2)=[C:5]([O:29]COC)[CH:4]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[C:14]=3[N:15]=2)=[C:5]([OH:29])[CH:4]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 219593292-(4,5-Dimethoxy-2-methoxymethoxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole

Product 1

HCID 1354286942-(4,5-Dimethoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl) aminomethylbenzoxazoleYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7 (100 mg, 0.23 mmol) and p-toluenesulfonic acid monohydrate (190 mg, 1 mmol) in methanol (20 mL) was stirred overnight at room temperature. After the solvent was evaporated, ethyl acetate (20 mL) was added to the resulting residue which was neutralized by Na2CO3, washed with brine and water, dried over MgSO4, and concentrated in vacuo to give a pale yellow solid that was purified by silica gel column chromatography (ethyl acetate) and crystallized from ethanol to afford a white solid of Zinbo-5 (80 mg, 89%): 1H-NMR (500 MHz, CDCl3) δ3.95 (s, 3H), 3.96 (s, 3H), 4.01 (s, 2H), 4.21 (s, 2H), 6.66 (s, 1H), 7.17 (dd, 1H, J=7.5, 5.0 Hz), 7.31 (t, 1H, J=8.0 Hz), 7.37–7.40 (m, 2H), 7.41 (s, 1H), 7.48 (d, 1H, J=8.0 Hz),7.67 (t, 1H, J=7.5 Hz), 8.66 (d, 2H, J=5.0 Hz), 11.27 (s, 1H); Anal. Calcd for C22H21N3O4: C, 67.51; H, 5.41; N, 10.74. Found: C, 67.12; H, 5.25; N, 10.57.

Workup

  1. customAfter the solvent was evaporated
  2. additionethyl acetate (20 mL) was added to the resulting residue which
  3. washwashed with brine and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a pale yellow solid
  7. customthat was purified by silica gel column chromatography (ethyl acetate)
  8. customcrystallized from ethanol

Sources & evidence

ORD record
ord-9fc356e668894dacac6ca500fdfd939b
Source dataset
uspto-grants-2006_09
Patent number
US07105680B1

Reaction notes

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