Water → HCID 178482114, compound

HRID 1262335Notes

Reaction equation

HRID 1262335 reaction equation
CS([C:4]1[N:9]=[CH:8][C:7]2=[C:10]([O:25][CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])[N:6]2[N:5]=1)=O.[OH-:34].[Na+].O>C(O)(=O)C>[OH:34][C:4]1[N:9]=[CH:8][C:7]2=[C:10]([O:25][CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:32])([CH3:33])[CH3:31])[CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])[N:6]2[N:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 66711169N-{2-[2-Methanesulfinyl-5-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methane sulfonamide

Product 1

HCID 178482114HCID 178482114, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

Into a 8-dram vial, N-{2-[2-Methanesulfinyl-5-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methane sulfonamide (480 mg, 0.94 mmol) was added to heated solution of 19.10 M of Sodium hydroxide in Water (5.0 mL, 96 mmol) at 110° C. The reaction mixture was heated at 120° C. for 2 hours. 5 mL of Acetic acid was added to adjust pH to 5. The reaction was partitioned with water and DCM. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum. The reaction mixture was purified via ISCO column chromatography with DCM and NH3 in methanol as eluant (2 to 15% methanol). The collected fractions afforded N-{2-[2-Hydroxy-5-(2-trimethylsilanyl-ethoxymethoxy)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methanesulfonamide as a red solid (195 mg, 45%).

Workup

  1. customThe reaction was partitioned with water and DCM
  2. customThe organic was separated
  3. washwashed with Brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe solid was filtered
  6. washwashed with DCM
  7. customThe solvent was removed under vacuum
  8. customThe reaction mixture was purified via ISCO column chromatography with DCM and NH3 in methanol as eluant (2 to 15% methanol)

Sources & evidence

ORD record
ord-1b37cdd9346b471c9a364f439a1827ab
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…