P-Toluenesulfonylhydrazide → HCID 18512161, compound

HRID 1370811Notes

Reaction equation

HRID 1370811 reaction equation
[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:9]1[C:10]([CH:20]=[CH2:21])=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(NN)(=O)=O)=CC=1.O.O.O.C([O-])(=O)C.[Na+]>COCCOC.O>[CH2:22]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[C:10]([CH2:20][CH3:21])=[C:11]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])[CH:12]=[CH:13][CH:14]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 15303P-ToluenesulfonylhydrazideHCID 18512405HCID 18512405, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 18512161HCID 18512161, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

The product from Example 44D (0.040 g, 0.102 mmoles) and p-toluenesulfonhydrazide (0.150 g, 1.02 mmoles) in ethylene glycol dimethyl ether (5 mL) at reflux were treated dropwise over a four hour period with a solution of sodium acetate trihydrate (0.232 g, 1.70 mmoles) in water. After the addition, the reaction mixture was allowed to cool to room temperature, poured into water and extracted with methylene chloride (3×). The extracts were combined, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC (CH3CN:0.1% TFA in H2O) on a YMC ODS Guardpak column. 1H NMR (300 MHz, CDCl3) δ7.32 (dd, J=8.0, 1.2 Hz, 1H), 7.35-7.15 (m, 11H), 7.09 (dd, J=8.0, 1.2 Hz, 1H), 6.14 (s, 1H), 4.09 (s, 4H), 2.85 (s, 3H), 2.74 (q, J=7.6 Hz, 2H), 1.00 (t, J=7.6 Hz, 3H); MS (ESI+) m/z 395 (M+H)+.

Workup

  1. additionAfter the addition
  2. extractionextracted with methylene chloride (3×)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative HPLC (CH3CN:0.1% TFA in H2O) on a YMC ODS Guardpak column

Sources & evidence

ORD record
ord-d6e51ea979e24f839eaec2b1e0a8c94a
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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