4-Methoxypyridine-3-boronic acid → 5-({4-[({[5-(4-Methoxypyridin-3-yl)-1H-indazol-3-yl]carbonyl}amino)methyl]piperidin-1-yl}methyl)furan-2-carboxylic acid formate

HRID 1752528Notes

Reaction equation

HRID 1752528 reaction equation
O.FC1C(F)=CC=CC=1C1C=C2C(=CC=1)NN=C2C(NCC1CCN(CC2OC=C([C:35]([OH:37])=[O:36])N=2)CC1)=O.Br[C:39]1[CH:40]=[C:41]2[C:45](=[CH:46][CH:47]=1)[NH:44][N:43]=[C:42]2[C:48]([NH:50][CH2:51][CH:52]1[CH2:57][CH2:56][N:55]([CH2:58][C:59]2[O:63][C:62]([C:64]([O:66]CC)=[O:65])=[CH:61][CH:60]=2)[CH2:54][CH2:53]1)=[O:49].[CH3:69][O:70][C:71]1[CH:76]=[CH:75][N:74]=[CH:73][C:72]=1B(O)O>>[CH:35]([OH:37])=[O:36].[CH3:69][O:70][C:71]1[CH:76]=[CH:75][N:74]=[CH:73][C:72]=1[C:39]1[CH:40]=[C:41]2[C:45](=[CH:46][CH:47]=1)[NH:44][N:43]=[C:42]2[C:48]([NH:50][CH2:51][CH:52]1[CH2:57][CH2:56][N:55]([CH2:58][C:59]2[O:63][C:62]([C:64]([OH:66])=[O:65])=[CH:61][CH:60]=2)[CH2:54][CH2:53]1)=[O:49]

Participants

4

Reactant 3

HCID 27625564-Methoxypyridine-3-boronic acidHCID 89767382HCID 89767382, compoundHCID 897676352-({4-[({[5-(2,3-Difluorophenyl)-1H-indazol-3-yl]carbonyl}amino)methyl]piperidin-1-yl}methyl)-1,3-oxazole-4-carboxylic acid hydrate

Product 1

HCID 897674655-({4-[({[5-(4-Methoxypyridin-3-yl)-1H-indazol-3-yl]carbonyl}amino)methyl]piperidin-1-yl}methyl)furan-2-carboxylic acid formate

Procedure

5-({4-[({[5-(4-Methoxypyridin-3-yl)-1H-indazol-3-yl]carbonyl}amino)methyl]piperidin-1-yl}methyl)furan-2-carboxylic acid formate 21 was prepared, according to the procedure described for compound 12, from compound 15 and (4-methoxypyridin-3-yl)boronic acid and using the following preparative HPLC parameters for the purification: channel A=CH3CN+0.1% formic acid; channel B=H2O+0.1% formic acid: flow=40 ml/min; gradient=2%-40% of eluent A in 15 minutes. Yield: 40 mg, 14%.

Workup

  1. customfor the purification

Sources & evidence

ORD record
ord-5868dc5efffb4590817e422bcc510d00
Source dataset
uspto-grants-2015_10
Patent number
US09163013B2

Reaction notes

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