4-Bromo-N-[methyl(oxo)pyrrolidin-1-yl-lambda6-sulfanylidene]aniline → (3R,3aR,6R,6aR)-6-({6-Chloro-5-[4-(4-{[methyl(oxo)pyrrolidin-1-yl-lambda6-sulfanylidene]amino}phenyl)phenyl]-3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridin-2-yl}oxy)-hexahydrofuro[3,2-b]furan-3-ol

HRID 1485618Notes

Reaction equation

HRID 1485618 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:25]=[C:24]([O:26][C@H:27]3[C@H:31]4[O:32][CH2:33][C@@H:34]([OH:35])[C@H:30]4[O:29][CH2:28]3)[N:23]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11](B2OC(C)(C)C(C)(C)O2)=[CH:10][CH:9]=1.Br[C:45]1[CH:59]=[CH:58][C:48]([N:49]=[S:50]([CH3:57])(=[O:56])[N:51]2[CH2:55][CH2:54][CH2:53][CH2:52]2)=[CH:47][CH:46]=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[N:25]=[C:24]([O:26][C@H:27]3[C@H:31]4[O:32][CH2:33][C@@H:34]([OH:35])[C@H:30]4[O:29][CH2:28]3)[N:23]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:42])([CH3:43])[CH3:41])[C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:45]2[CH:59]=[CH:58][C:48]([N:49]=[S:50]([CH3:57])(=[O:56])[N:51]3[CH2:55][CH2:54][CH2:53][CH2:52]3)=[CH:47][CH:46]=2)=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 1188639314-Bromo-N-[methyl(oxo)pyrrolidin-1-yl-lambda6-sulfanylidene]anilineHCID 123678375(3R,3aR,6R,6aR)-6-(6-Chloro-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol

Product 1

HCID 131736740(3R,3aR,6R,6aR)-6-({6-Chloro-5-[4-(4-{[methyl(oxo)pyrrolidin-1-yl-lambda6-sulfanylidene]amino}phenyl)phenyl]-3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridin-2-yl}oxy)-hexahydrofuro[3,2-b]furan-3-ol

Procedure

The title compound is prepared from (3R,3aR,6R,6aR)-6-(6-chloro-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol and 4-bromo-N-[methyl-(oxo)pyrrolidin-1-yl-λ6-sulfanylidene]aniline following a procedure analogous to that described for Intermediate 3 (Step 3). LC (method 1): tR=1.16 min; Mass spectrum (ESI+): m/z=726 [M+H]+.

Sources & evidence

ORD record
ord-0794b760bc3b4e5fb26f0b77d5f0cbd2
Source dataset
uspto-grants-2016_08
Patent number
US09422312B2

Reaction notes

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