(3R,3aR,6R,6aR)-6-(6-chloro-5-iodo-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol → N'-[4-(2-{[(3R,3aR,6R,6aR)-6-Hydroxy-hexahydrofuro[3,2-b]furan-3-yl]oxy}-6-chloro-3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridin-5-yl)phenyl]-N,N-dimethyl-methanesulfonimidamide

HRID 1485646Notes

Reaction equation

HRID 1485646 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:11]=[C:10]([O:12][C@H:13]3[C@H:17]4[O:18][CH2:19][C@@H:20]([OH:21])[C@H:16]4[O:15][CH2:14]3)[N:9]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:5]2=[N:6][C:7]=1I.[CH3:30][N:31]([CH3:51])[S:32]([CH3:50])(=[N:34][C:35]1[CH:40]=[CH:39][C:38](B2OC(C)(C)C(C)(C)O2)=[CH:37][CH:36]=1)=[O:33]>O1CCOCC1>[OH:21][C@H:20]1[C@H:16]2[O:15][CH2:14][C@@H:13]([O:12][C:10]3[N:9]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:5]4=[N:6][C:7]([C:38]5[CH:37]=[CH:36][C:35]([N:34]=[S:32]([CH3:50])([N:31]([CH3:30])[CH3:51])=[O:33])=[CH:40][CH:39]=5)=[C:2]([Cl:1])[CH:3]=[C:4]4[N:11]=3)[C@H:17]2[O:18][CH2:19]1

Participants

4

Reactant 2

HCID 123413447(3R,3aR,6R,6aR)-6-(6-chloro-5-iodo-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-olHCID 131736751N,N-Dimethyl-N'-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonimidamide

Product 1

HCID 131736752N'-[4-(2-{[(3R,3aR,6R,6aR)-6-Hydroxy-hexahydrofuro[3,2-b]furan-3-yl]oxy}-6-chloro-3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridin-5-yl)phenyl]-N,N-dimethyl-methanesulfonimidamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound is prepared from (3R,3aR,6R,6aR)-6-(6-chloro-5-iodo-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol and N,N-dimethyl-N′-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-methanesulfonimidamide following a procedure analogous to that described for Intermediate 3 (Step 3) using 1,4-dioxane as a solvent. LC (method 2): tR=1.00 min; Mass spectrum (ESI+): m/z=624 [M+H]+.

Sources & evidence

ORD record
ord-1cb733ce329b41b691127740837fa6e7
Source dataset
uspto-grants-2016_08
Patent number
US09422312B2

Reaction notes

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