Sodium Methoxide → HCID 11620207, compound

HRID 1042646Notes

Reaction equation

HRID 1042646 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13](F)=[C:14]([CH:34]=2)[C:15]([NH:17][C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:19]=2[N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[O:16])=[CH:4][N:3]=1.[CH3:36][O-:37].[Na+]>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([O:37][CH3:36])=[C:14]([CH:34]=2)[C:15]([NH:17][C:18]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:19]=2[N:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[O:16])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 10942334Sodium MethoxideHCID 16109018HCID 16109018, compound

Product 1

HCID 11620207HCID 11620207, compound

Procedure

A mixture of 5-(2-(2-aminopyrimidin-5-yl)ethynyl)-2-fluoro-N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide (0.14 g, 0.29 mmol) and NaOMe (0.5 M solution in methanol, 2.0 mL, 1.0 mmol) in a sealed tube was heated to reflux. After 16 h, the reaction was cooled and partitioned between EtOAc and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The material was purified by preparative TLC, eluting with 30% acetone/dichloromethane to give 5-(2-(2-aminopyrimidin-5-yl)ethynyl)-2-methoxy-N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide as a white solid. MS m/z=496 [M+H]+. Calc'd for C26H24F3N5O2: 495.

Workup

  1. temperaturewas heated to reflux
  2. temperaturethe reaction was cooled
  3. custompartitioned between EtOAc and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by preparative TLC
  8. washeluting with 30% acetone/dichloromethane

Sources & evidence

ORD record
ord-9d384534050642f5a3bb2b48f9de4ce6
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

Loading…