(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 → 1-(4-(6-Chloro-2-((3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yloxy)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-5-yl)phenyl)piperidin-4-yl dimethylcarbamate

HRID 715562Notes

Reaction equation

HRID 715562 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]([CH3:56])[C:32](=[O:55])[O:33][CH:34]1[CH2:39][CH2:38][N:37]([C:40]2[CH:45]=[CH:44][C:43](B3OC(C)(C)C(C)(C)O3)=[CH:42][CH:41]=2)[CH2:36][CH2:35]1>>[CH3:30][N:31]([CH3:56])[C:32](=[O:55])[O:33][CH:34]1[CH2:39][CH2:38][N:37]([C:40]2[CH:45]=[CH:44][C:43]([C:7]3[N:6]=[C:5]4[N:9]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:10]([O:12][C@@H:13]5[CH2:14][O:15][C@@H:16]6[C@H:20]([OH:21])[CH2:19][O:18][C@H:17]56)=[N:11][C:4]4=[CH:3][C:2]=3[Cl:1])=[CH:42][CH:41]=2)[CH2:36][CH2:35]1

Participants

3

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 1237646031-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidin-4-yl dimethylcarbamate

Product 1

HCID 1234386321-(4-(6-Chloro-2-((3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yloxy)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-5-yl)phenyl)piperidin-4-yl dimethylcarbamate

Procedure

The title compound is prepared from (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 and 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidin-4-yl dimethylcarbamate following a procedure analogous to that described for Intermediate 3. LC (method 1): tR=1.04 min; Mass spectrum (ESI+): m/z=674 [M+H]+.

Sources & evidence

ORD record
ord-e3afc787da1449d8954ced4c9ed7b266
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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