Methanol → HCID 69522772, compound

HRID 1181446Notes

Reaction equation

HRID 1181446 reaction equation
[H-].[Na+].[CH:3]1[C:12]2[C:7](=[C:8]([NH:13][C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)=[O:15])[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1.[CH3:28]I.CO>C1COCC1.C(Cl)Cl>[CH:3]1[C:12]2[C:7](=[C:8]([N:13]([CH3:28])[C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:20][CH:19]=3)=[O:15])[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 8068410A-425619

Product 1

HCID 69522772HCID 69522772, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in oil, 7 mg, 0.17 mmol) was added to a suspension N-isoquinolin-5-yl-N′-[4-(trifluoromethyl)benzyl]urea (Example 14; 48 mg, 0.14 mmol) in THF (3 mL) at room temperature and the reaction was stirred until effervescence ceased (20 minutes). Methyl iodide (11 μL, 0.17 mmol) was added and the reaction stirred at room temperature for 3 hours. TLC analysis (10% MeOH in CH2Cl2) indicated only one major product. The reaction was evaporated in vacuo and the product isolated by preparative TLC (4% MeOH in CH2Cl2) to give the title compound. m/z (ES+) 360 (M+H)+.

Workup

  1. custom(20 minutes)
  2. stirringthe reaction stirred at room temperature for 3 hours
  3. customThe reaction was evaporated in vacuo
  4. customthe product isolated by preparative TLC (4% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-fc8d90e57832447e86951084d3bdb318
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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