Water → HCID 57799780, compound

HRID 2101101Notes

Reaction equation

HRID 2101101 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:11])[O:8][CH:7]([CH2:9][OH:10])[CH2:6][O:5]1.[Cl:12][C:13]1[C:22]2[C:17](=[CH:18][C:19](F)=[C:20]([O:23][CH2:24][CH2:25][O:26][CH3:27])[CH:21]=2)[CH:16]=[C:15]([NH:29][C:30]2[CH:34]=[C:33]([CH3:35])[NH:32][N:31]=2)[N:14]=1.O>CN(C=O)C>[Cl:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:10][CH2:9][CH:7]3[CH2:6][O:5][C:4]([CH3:11])([CH3:3])[O:8]3)=[C:20]([O:23][CH2:24][CH2:25][O:26][CH3:27])[CH:21]=2)[CH:16]=[C:15]([NH:29][C:30]2[CH:34]=[C:33]([CH3:35])[NH:32][N:31]=2)[N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7528SolketalHCID 24758Sodium hydrideHCID 57799490HCID 57799490, compound

Product 1

HCID 57799780HCID 57799780, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

NaH (150 mg) was carefully added to the solution of (2,2-Dimethyl-[1,3]dioxolan-4-yl)-methanol (0.3 ml) in DMF (2 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. for 1 hour. The mixture was poured into 50 ml of water. The mixture was extracted by ethyl acetate (50 ml×3). The organic layer was evaporated to give [1-Chloro-6-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-7-(2-methoxy-ethoxy)-isoquinolin-3-yl]-(5-methyl-1H-pyrazol-3-yl)-amine as oil (100 mg). LC-MS: m/e 463(MH+).

Workup

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

Sources & evidence

ORD record
ord-50fe5fa3d62c443388b83f13cdb5d3b4
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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