HCID 68772801, compound → HCID 68777421, compound

HRID 2191092Notes

Reaction equation

HRID 2191092 reaction equation
[CH3:1][C:2]1([CH3:40])[CH2:38][C:6]2[C:7]([C:16]3[CH:21]=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:19]=[C:18]([O:28]CC4C=CC(OC)=CC=4)[CH:17]=3)=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[S:9][C:5]=2[C:4](=[O:39])[CH2:3]1>FC(F)(F)C(O)=O>[CH3:1][C:2]1([CH3:40])[CH2:38][C:6]2[C:7]([C:16]3[CH:21]=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[NH:19][C:18](=[O:28])[CH:17]=3)=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[S:9][C:5]=2[C:4](=[O:39])[CH2:3]1

Participants

3

Reactant 1

HCID 68772801HCID 68772801, compound

Product 1

HCID 68777421HCID 68777421, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of Example 339 (36 mg, 0.065 mmol) in trifluoroacetic acid (10 mL) was heated at reflux for 4 h. The solvent was removed in vacuo and the residue was purified by column chromatography (SiO2, 0-100% EtOAc/heptane) to give the title compound (12 mg, 42%) as an off-white solid. δH (CDCl3) 7.70-7.64 (2H, m), 7.58-7.52 (3H, m), 6.70 (1H, d, J 1.3 Hz), 6.46 (1H, d, J 1.3 Hz), 3.77-3.70 (4H, m), 3.17-3.11 (4H, m), 2.61 (2H, s), 2.45 (2H, s), 1.07 (6H, s). LCMS (ES+) 435.3 (M+H)+.

Workup

  1. temperatureat reflux for 4 h
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography (SiO2, 0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-4da5ce374a29435f894b85096002de8a
Source dataset
uspto-grants-2012_12
Patent number
US08324204B2

Reaction notes

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