HCID 118863939, compound → HCID 131736749, compound

HRID 1485643Notes

Reaction equation

HRID 1485643 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:50]=[CH:49][C:48]([CH2:51][N:52]=[S:53]([CH3:60])(=[O:59])[N:54]2[CH2:58][CH2:57][CH2:56][CH2:55]2)=[CH:47][CH:46]=1>O1CCOCC1>[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:9]=[CH:10][C:11]([C:45]2[CH:50]=[CH:49][C:48]([CH2:51][N:52]=[S:53]([CH3:60])(=[O:59])[N:54]3[CH2:58][CH2:57][CH2:56][CH2:55]3)=[CH:47][CH:46]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 118863939HCID 118863939, compoundHCID 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 131736749HCID 131736749, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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-bromophenyl)-methyl][methyl(oxo)pyrrolidin-1-yl-λ6-sulfanylidene]amine following a procedure analogous to that described for Intermediate 3 (Step 3) using 1,4-dioxane as a solvent. LC (method 1): tR=1.05 min; Mass spectrum (ESI+): m/z=740 [M+H]+.

Sources & evidence

ORD record
ord-9b206e8a86aa4fcf9edfe47fa9b230c7
Source dataset
uspto-grants-2016_08
Patent number
US09422312B2

Reaction notes

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