3-(4-Chloro-7-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[3,2-d]pyrimidin-5-yl)propane-1,2-diol → (4-chloro-7-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[3,2-d]pyrimidin-5-yl)acetaldehyde

HRID 244457Notes

Reaction equation

HRID 244457 reaction equation
[Cl:1][C:2]1[C:3]2[N:10]([CH2:11][CH:12]([OH:15])CO)[CH:9]=[C:8]([C:16]([C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[N:26]=[CH:25]4)([OH:21])[C:17]([F:20])([F:19])[F:18])[C:4]=2[N:5]=[CH:6][N:7]=1>CC(C)=O.O>[Cl:1][C:2]1[C:3]2[N:10]([CH2:11][CH:12]=[O:15])[CH:9]=[C:8]([C:16]([C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)[N:26]=[CH:25]4)([OH:21])[C:17]([F:20])([F:19])[F:18])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 1

HCID 249579933-(4-Chloro-7-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[3,2-d]pyrimidin-5-yl)propane-1,2-diol

Product 1

HCID 59437308(4-chloro-7-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[3,2-d]pyrimidin-5-yl)acetaldehyde

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a room temperature solution of 3-(4-chloro-7-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[3,2-d]pyrimidin-5-yl)propane-1,2-diol (95 mg, 0.18 mmol, 1 equiv.) in 3 mL of acetone and 1 mL of water was added NaIO4 (120 mg, 0.56 mmol, 4 equiv.). After 3 days, the mixture was filtered and the filtrate concentrated to near dryness. The residue was diluted with water and extracted with EtOAc. The combined organic layers were dried, filtered and concentrated in vacuo to afford (4-chloro-7-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[3,2-d]pyrimidin-5-yl)acetaldehyde which was used without further purification.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate concentrated
  3. additionThe residue was diluted with water
  4. extractionextracted with EtOAc
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a2cb88b9e6446a88c3fc0fcba95a4c1
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

Loading…