m-Chloroperbenzoic acid → HCID 68431404, compound

HRID 2092087Notes

Reaction equation

HRID 2092087 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[O:11])[N:5]=[CH:4][C:3]=1[NH:20][C@@H:21]1[CH2:26][C@@H:25]2[CH2:27][C@@H:23]([C:24]2([CH3:29])[CH3:28])[C@H:22]1[CH3:30].ClC1C=CC=C(C(OO)=[O:39])C=1>O1CCCC1>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:15]=[CH:16][N+:17]([O-:39])=[CH:18][CH:19]=2)=[O:11])[N:5]=[CH:4][C:3]=1[NH:20][C@@H:21]1[CH2:26][C@@H:25]2[CH2:27][C@@H:23]([C:24]2([CH3:29])[CH3:28])[C@H:22]1[CH3:30]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68430690HCID 68430690, compound

Product 1

HCID 68431404HCID 68431404, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

2-{5-Bromo-6-oxo-4-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-1(6H)-yl}-N-(pyridin-4-ylmethyl)acetamide (50 mg, 0.105 mmol) and m-chloroperbenzoic acid (35 mg, 0.112 mmol) suspended in tetrahydrofuran (1.5 mL) were stirred at room temperature for 5 minutes and at 80° C. for 30 minutes. After cooling, the reaction solution was concentrated, and the resulting residue was purified by silica gel chromatography (chloroform/methanol=5/1) to give the desired product (49 mg, 95% yield).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction solution was concentrated
  3. customthe resulting residue was purified by silica gel chromatography (chloroform/methanol=5/1)

Sources & evidence

ORD record
ord-3f5e34b91b174b2eb128dfa741b1b2ca
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

Loading…