Diazabicyclo[5.4.0]undec-7-ene → 2-(((3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)oxy)-6-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridine

HRID 929186Notes

Reaction equation

HRID 929186 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[N:8]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:9](S(C)(=O)=O)=[N:10][C:4]=2[CH:3]=1.[Si:23]([O:30][C@H:31]1[C@H:35]2[O:36][CH2:37][C@@H:38]([OH:39])[C@H:34]2[O:33][CH2:32]1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].N12CCCC=C1CCCCN2>CN(C=O)C>[Si:23]([O:30][C@H:31]1[C@H:35]2[O:36][CH2:37][C@@H:38]([O:39][C:9]3[N:8]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:5]4[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][C:4]=4[N:10]=3)[C@H:34]2[O:33][CH2:32]1)([C:26]([CH3:29])([CH3:27])[CH3:28])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 9834010Diazabicyclo[5.4.0]undec-7-eneHCID 67050109(3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-olHCID 900421456-chloro-2-(methylsulfonyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridine

Product 1

HCID 900421802-(((3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)oxy)-6-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 6-chloro-2-(methylsulfonyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridine (100 mgs, 0.276 mmol) and (3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-ol (72.0 mg, 0.276 mmol) in anhydrous DMF (2.3 mL) was added diazabicyclo[5.4.0]undec-7-ene (DBU, 0.06 mL, 0.42 mmol). The reaction was stirred under N2 at RT for 20 h, then evaporated under reduced pressure. Flash chromatography of the resulting residue utilizing a 24 g silica RediSep Rf® Gold column and employing a 0-90% EtOAc/hexane gradient afforded the title compound. LC-MS: calculated for C24H40ClN3O5Si2 541.22 observed m/e: 542.08 (M+H)+ (Rt 1.74/2.0 min)

Workup

  1. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-080463d8553b47a1a19a5cfcf7a581fb
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

Loading…