Water → HCID 57799541, compound

HRID 2101100Notes

Reaction equation

HRID 2101100 reaction equation
[H-].[Na+].[O:3]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4]1.[Cl:9][C:10]1[C:19]2[C:14](=[CH:15][C:16](F)=[C:17]([O:20][CH2:21][CH2:22][O:23][CH3:24])[CH:18]=2)[CH:13]=[C:12]([NH:26][C:27]2[CH:31]=[C:30]([CH3:32])[NH:29][N:28]=2)[N:11]=1.O>CN(C=O)C>[Cl:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:8][CH:5]3[CH2:6][CH2:7][O:3][CH2:4]3)=[C:17]([O:20][CH2:21][CH2:22][O:23][CH3:24])[CH:18]=2)[CH:13]=[C:12]([NH:26][C:27]2[CH:31]=[C:30]([CH3:32])[NH:29][N:28]=2)[N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 99603-Furanol, tetrahydro-HCID 24758Sodium hydrideHCID 57799490HCID 57799490, compound

Product 1

HCID 57799541HCID 57799541, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

NaH (70 mg) was carefully added to a solution of tetrahydro-furan-3-ol (0.2 ml) in DMF (3 ml) and the mixture was stirred for 1 hour. [1-Chloro-6-fluoro-7-(2-methoxy-ethoxy)-isoquinolin-3-yl]-(5-methyl-1H-pyrazol-3-yl)-amine (100 mg) was added under N2, and the mixture was heated at 90° C. overnight. The mixture was poured to 50 ml of water. The mixture was extracted by ethyl acetate (50 ml×3). The organic layer was evaporated to give [1-Chloro-7-(2-methoxy-ethoxy)-6-(tetrahydro-furan-3-yloxy)-isoquinolin-3-yl]-(5-methyl-1H-pyrazol-3-yl)-amine as oil (100 mg). LC-MS: m/e 419(MH+).

Workup

  1. extractionThe mixture was extracted by ethyl acetate (50 ml×3)
  2. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-d17a7890e9d04341ac539aecbd9edc8e
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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