Water → HCID 10338335, compound

HRID 1445517Notes

Reaction equation

HRID 1445517 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:9]2[CH:10]=[C:11]([O:15][CH:16]([CH3:18])[CH3:17])[C:12]([NH2:14])=[CH:13][C:8]=2[O:7][C:6]=1[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[O:4].[CH2:26](N(CC)CC)C.COS(OC)(=O)=O.O>C(OCC)C>[CH3:1][NH:2][C:3]([C:5]1[C:9]2[CH:10]=[C:11]([O:15][CH:16]([CH3:18])[CH3:17])[C:12]([NH:14][CH3:26])=[CH:13][C:8]=2[O:7][C:6]=1[C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 10450038HCID 10450038, compound

Product 1

HCID 10338335HCID 10338335, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6-Amino-2-(4-fluoro-phenyl)-5-isopropoxy-benzofuran-3-carboxylic acid methylamide, prepared according to Example 16 (55 mg, 161 μmol) was dissolved in anhydrous diethyl ether (2 mL). Triethylamine (25 μL, 193 μmol) was added to the reaction mixture, followed by the slow addition of dimethylsulfate (17 μL, 177 μmol). Water (1 mL) was added after 2 hours. The reaction was concentrated to dryness, and the crude product was purified on HPLC (reverse phase) to provide 32 mg (56%) of pure product.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. customthe crude product was purified on HPLC (reverse phase)

Sources & evidence

ORD record
ord-dbe35d33412a4e9c82a93c8ba23ee09b
Source dataset
uspto-grants-2010_02
Patent number
US07666863B2

Reaction notes

Loading…