Trifluoroacetic acid → (3R,3aR,6R,6aR)-6-((6-chloro-5-(3,6-dihydro-2H-thiopyran-4-yl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol

HRID 929256Notes

Reaction equation

HRID 929256 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:16](COCC[Si](C)(C)C)[C:15]([O:25][C@H:26]3[C@H:30]4[O:31][CH2:32][C@@H:33]([OH:34])[C@H:29]4[O:28][CH2:27]3)=[N:14][C:5]2=[N:6][C:7]=1[C:8]1[CH2:9][CH2:10][S:11][CH2:12][CH:13]=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[NH:16][C:15]([O:25][C@H:26]3[C@H:30]4[O:31][CH2:32][C@@H:33]([OH:34])[C@H:29]4[O:28][CH2:27]3)=[N:14][C:5]2=[N:6][C:7]=1[C:8]1[CH2:13][CH2:12][S:11][CH2:10][CH:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 90041813(3R,3aR,6R,6aR)-6-((6-chloro-5-(3,6-dihydro-2H-thiopyran-4-yl)-1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol

Product 1

HCID 90067601(3R,3aR,6R,6aR)-6-((6-chloro-5-(3,6-dihydro-2H-thiopyran-4-yl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (3R,3aR,6R,6aR)-6-((6-chloro-5-(3,6-dihydro-2H-thiopyran-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol (74 mg, 0.141 mmol) in anhydrous DCM (0.45 mL) was added TFA (0.45 mL, 5.84 mmol). The solution stirred at RT for 18 h. The reaction solution was added to saturated NaHCO3 (35 mL) and extracted with EtOAc (2×45 mL). The organic layers combined, dried over Na2SO4, filtered, and the filtrate evaporated under reduced pressure. Flash chromatography utilizing a 12 g silica RediSep Rf® Gold column and employing a 0-10% MeOH/DCM gradient afforded the title compound. LC-MS: calculated for C17H18ClN3O4S 395.07 observed m/e: 395.90 (M+H)+ (Rt 0.84/2.0 min)

Workup

  1. extractionextracted with EtOAc (2×45 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-efe0960a906e4587a421f73ff82db798
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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