Formic Acid → HCID 90077264, compound

HRID 1050258Notes

Reaction equation

HRID 1050258 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:22](COCC[Si](C)(C)C)[C:21]([O:31][C@H:32]3[CH2:41][O:40][C@H:39]4[C@@H:34]([O:35]C(C5C=CC=CC=5)[O:37][CH2:38]4)[CH2:33]3)=[N:20][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][Si](C)(C)C)=[CH:10][CH:9]=1.C(O)=O.S([O-])(O)(=O)=O.[K+].[OH-].[Na+]>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[NH:22][C:21]([O:31][C@H:32]3[CH2:41][O:40][C@H:39]([CH2:38][OH:37])[C@@H:34]([OH:35])[CH2:33]3)=[N:20][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]#[CH:15])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 90077288HCID 90077288, compound

Product 1

HCID 90077264HCID 90077264, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6-chloro-2-(((4aR,7R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)oxy)-1-((2-(trimethylsilyl)ethoxy)methyl)-5-(4-((trimethylsilyl)ethynyl)phenyl)-1H-imidazo[4,5-b]pyridine (220 mg, 0.319 mmol) was dissolved in formic Acid (4.5 ml, 117 mmol) and sat. potassium hydrogen sulfate (0.5 ml, 0.319 mmol). The mixture was stirred at rt for 1 h, and then diluted with EtOAc. Then 3 M NaOH was added until a pH of pH 14 was reached. The mixture was stirred for 15 minutes at rt and then the layers were separated. The aqueous phase was extracted with EtOAc (×2). The combined organic extracts were washed with brine and dried over Na2SO4, filtered and concentrated. The resulting crude product was purified by column chromatography on Biotage™ 25 g column by eluting with 50% EtOAc in DCM to yield the title compound. LC-MS: m/e=400.32 (M+H)+ (Rt 1.71/4 min).

Workup

  1. stirringThe mixture was stirred for 15 minutes at rt
  2. customthe layers were separated
  3. extractionThe aqueous phase was extracted with EtOAc (×2)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting crude product was purified by column chromatography on Biotage™ 25 g column
  9. washby eluting with 50% EtOAc in DCM

Sources & evidence

ORD record
ord-2dfa8a2a35c54865aedfb606eb910651
Source dataset
uspto-grants-2016_07
Patent number
US09382243B2

Reaction notes

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