Methanol → HCID 59168330, compound

HRID 2195045Notes

Reaction equation

HRID 2195045 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:18][CH2:17][CH2:16][CH:15]3[CH3:19])[N:11]=[C:10]([N:20]3[CH2:25][CH2:24][N:23]([C:26]4[C:34]([CH3:35])=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][N:27]=4)[CH2:22][C@H:21]3[CH3:36])[CH:9]=2)=[CH:4][CH:3]=1.[CH3:37]O>OS(O)(=O)=O>[CH3:37][O:31][C:30](=[O:32])[C:29]1[CH:33]=[C:34]([CH3:35])[C:26]([N:23]2[CH2:24][CH2:25][N:20]([C:10]3[CH:9]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[N:13]=[C:12]([N:14]4[CH2:18][CH2:17][CH2:16][CH:15]4[CH3:19])[N:11]=3)[C@H:21]([CH3:36])[CH2:22]2)=[N:27][CH:28]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 11554952HCID 11554952, compound

Product 1

HCID 59168330HCID 59168330, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

Reflux a solution of 6-{4-[6-(4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-(R)-methyl-piperazin-1-yl}-5-methyl-nicotinic acid (120 mg, 0.245 mmol) and 2 drops of concentrated H2SO4 in MeOH for 4 h. Cool to room temperature, concentrate, and partition between saturated NaHCO3 and EtOAc. Dry the solution (Na2SO4), concentrate under reduced pressure. Purify the residue by flash column chromatography eluting with EtOAc-Hexanes (1:4) to afford the title ester as an oil.

Workup

  1. concentrationconcentrate
  2. custompartition between saturated NaHCO3 and EtOAc
  3. dry with materialDry the solution (Na2SO4)
  4. concentrationconcentrate under reduced pressure
  5. customPurify the residue by flash column chromatography
  6. washeluting with EtOAc-Hexanes (1:4)

Sources & evidence

ORD record
ord-d6f17ad229814a5b87949208930aba5a
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

Loading…