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

HRID 1752525Notes

Reaction equation

HRID 1752525 reaction equation
O.FC1C(F)=CC=CC=1C1C=C2C(=CC=1)NN=C2C(NCC1CCN(CC2OC=C(C(O)=O)N=2)CC1)=[O:20].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][C:74](B(O)O)=[CH:73][CH:72]=1>>[OH2:20].[CH3:69][O:70][C:71]1[CH:76]=[CH:75][C:74]([C:39]2[CH:40]=[C:41]3[C:45](=[CH:46][CH:47]=2)[NH:44][N:43]=[C:42]3[C:48]([NH:50][CH2:51][CH:52]2[CH2:57][CH2:56][N:55]([CH2:58][C:59]3[O:63][C:62]([C:64]([OH:66])=[O:65])=[CH:61][CH:60]=3)[CH2:54][CH2:53]2)=[O:49])=[CH:73][CH:72]=1

Participants

4

Reactant 3

HCID 201262(4-Methoxyphenyl)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 897672005-({4-[({[5-(4-Methoxyphenyl)-1H-indazol-3-yl]carbonyl}amino)methyl]piperidin-1-yl}methyl)furan-2-carboxylic acid hydrate

Procedure

5-({4-[({[5-(4-Methoxyphenyl)-1H-indazol-3-yl]carbonyl}amino)methyl]piperidin-1-yl}methyl)furan-2-carboxylic acid hydrate 18 was prepared, according to the procedure described for compound 12, from compound 15 and (4-methoxyphenyl)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=15%-50% of eluent A in 15 minutes. Yield: 14 mg, 5%.

Workup

  1. customfor the purification

Sources & evidence

ORD record
ord-49fc77fd91b6439daacaad6f89545c38
Source dataset
uspto-grants-2015_10
Patent number
US09163013B2

Reaction notes

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