p-Toluenesulfonic acid → HCID 59644208, compound

HRID 2252094Notes

Reaction equation

HRID 2252094 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=[C:27]([CH3:35])[CH:26]=3)[CH:19]=2)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1.[CH2:54](O)[CH2:55][CH2:56][OH:57]>CCOC(C)=O>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2([C:18]3[CH:19]=[C:20]([NH:24][C:25]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]=[C:27]([CH3:35])[CH:26]=4)[CH:21]=[CH:22][CH:23]=3)[O:57][CH2:56][CH2:55][CH2:54][O:17]2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 58958057HCID 58958057, compoundHCID 131726737HCID 131726737, compound

Product 1

HCID 59644208HCID 59644208, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the mixture of the compound of Example 209 (0.31 g, 0.67 mmol) in toluene/propane-1,3-diol (7 ml/7 ml) was added p-TsOH (0.32 g, 1.68 mmol) at room temperature. The resulting mixture was heated under reflux in a Dean-Stark setup overnight before the reaction was diluted with EtOAc (80 ml). The mixture was washed with 1 N NaOH (2×50 ml) and brine (50 ml). The organic layer was dried over Na2SO4 and concentrated on a rotavap to dryness. The residue was purified by reverse phase HPLC to afford the desired product as an off-white solid (74 mg, 42% with 50% starting material recovered). The compound of Example 348 was synthesized in the same manner as for Example 191 using 1-benzylpiperazine instead of compound 36.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux in a Dean-Stark setup overnight before the reaction
  3. washThe mixture was washed with 1 N NaOH (2×50 ml) and brine (50 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated on a rotavap to dryness
  6. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-ec1d20c185064bcd8cbd579f2e36ad58
Source dataset
uspto-grants-2008_01
Patent number
US07320989B2

Reaction notes

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