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

HRID 1485616Notes

Reaction equation

HRID 1485616 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.[N:44]1([S:48]([CH3:58])(=[O:57])=[N:49][C:50]2[CH:55]=[CH:54][C:53](Br)=[CH:52][CH:51]=2)[CH2:47][CH2:46][CH2:45]1>>[N:44]1([S:48](=[N:49][C:50]2[CH:55]=[CH:54][C:53]([C:11]3[CH:12]=[CH:13][C:8]([C:7]4[N:6]=[C:5]5[N:23]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:42])([CH3:41])[CH3:43])[C:24]([O:26][C@H:27]6[C@H:31]7[O:32][CH2:33][C@@H:34]([OH:35])[C@H:30]7[O:29][CH2:28]6)=[N:25][C:4]5=[CH:3][C:2]=4[Cl:1])=[CH:9][CH:10]=3)=[CH:52][CH:51]=2)([CH3:58])=[O:57])[CH2:45][CH2:46][CH2:47]1

Participants

3

Reactant 2

HCID 118863933N-[Azetidin-1-yl(methyl)oxo-lambda6-sulfanylidene]-4-bromoanilineHCID 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 131736739(3R,3aR,6R,6aR)-6-({5-[4-(4-{[Azetidin-1-yl(methyl)oxo-lambda6-sulfanylidene]-amino}phenyl)phenyl]-6-chloro-3-{[2-(trimethylsilyl)ethoxy]methyl}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 N-[azetidin-1-yl(methyl)oxo-λ6-sulfanylidene]-4-bromoaniline following a procedure analogous to that described for Intermediate 3 (Step 3). LC (method 1): tR=1.12 min; Mass spectrum (ESI+): m/z=712 [M+H]+.

Sources & evidence

ORD record
ord-790a80211262403e9c2a009469310fe7
Source dataset
uspto-grants-2016_08
Patent number
US09422312B2

Reaction notes

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