HCID 68817299, compound → HCID 11688866, compound

HRID 731978Notes

Reaction equation

HRID 731978 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([CH:12]([CH3:26])[N:13]([C:16](=[O:25])[C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=4)[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3.ClC1C=CC(C2C=CC=CC=2C(NC(=O)C2C=CC=C(OC)C=2)C)=C(F)C=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([CH:12]([CH3:26])[N:13]([C:16]([C:17]4[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=4)=[O:25])[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

3

Reactant 1

HCID 68817299HCID 68817299, compound

Product 1

HCID 11688866HCID 11688866, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

3-chloro-5-(3-methoxybenzoyl)-6-methyl-5,6-dihydrophenanthridine—N-[1-(4′-Chloro-2′-fluoro-biphenyl-2-yl)-ethyl]-3-methoxy-benzamide (1.04 g, 2.7 mmol) was dissolved in anhydrous THF (10 mL) and the vial was capped and purged with an inert atmosphere. Lithium bis(trimethylsilyl)amide (4.1 mL, 1M in THF) was added to the solution and the mixture heated (70° C). The reaction progress was monitored by LCMS and heating was discontinued upon the expense of the starting material. The THF was removed and the resulting residue was purified by flash column chromatography (Biotage® 40 Mi, 30-50% methyl tert-butylether in hexane) affording 537 mg (54%) of the desired product. MS [(ES+), m/z]: 364/366 [M+H]+, 1 Cl pattern.

Workup

  1. customthe vial was capped
  2. custompurged with an inert atmosphere
  3. additionLithium bis(trimethylsilyl)amide (4.1 mL, 1M in THF) was added to the solution
  4. temperatureheating
  5. customThe THF was removed
  6. customthe resulting residue was purified by flash column chromatography (Biotage® 40 Mi, 30-50% methyl tert-butylether in hexane)

Sources & evidence

ORD record
ord-8bda54e626f04ea38246d8afdaebbcd2
Source dataset
uspto-grants-2009_09
Patent number
US07585871B2

Reaction notes

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