4-Cyano-3-methoxyphenylboronic acid → 2-methoxy-4-(3-methyl-4-((R)-1-((R)-5-oxopyrrolidin-3-yl)ethoxy)-3H-imidazo[4,5-c]pyridin-6-yl)benzonitrile

HRID 2209048Notes

Reaction equation

HRID 2209048 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C@@H:9]([C@H:11]2[CH2:15][NH:14][C:13](=[O:16])[CH2:12]2)[CH3:10])[C:5]2[N:17]([CH3:20])[CH:18]=[N:19][C:4]=2[CH:3]=1.[C:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][C:24]=1[O:32][CH3:33])#[N:22]>C(#N)C1C=CC=CC=1>[CH3:33][O:32][C:24]1[CH:25]=[C:26]([C:2]2[N:7]=[C:6]([O:8][C@@H:9]([C@@H:11]3[CH2:12][C:13](=[O:16])[NH:14][CH2:15]3)[CH3:10])[C:5]3[N:17]([CH3:20])[CH:18]=[N:19][C:4]=3[CH:3]=2)[CH:27]=[CH:28][C:23]=1[C:21]#[N:22]

Participants

4

Reactant 2

HCID 450912364-Cyano-3-methoxyphenylboronic acidHCID 117843294(R)-4-((R)-1-((6-chloro-3-methyl-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one

Product 1

HCID 1178432282-methoxy-4-(3-methyl-4-((R)-1-((R)-5-oxopyrrolidin-3-yl)ethoxy)-3H-imidazo[4,5-c]pyridin-6-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 7505BenzonitrileSolvent

Procedure

Following General Procedure B, beginning with (R)-4-((R)-1-(6-chloro-3-methyl-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 2.06 (41 mg, 0.139 mmol) and 4-cyano-3-methoxyphenylboronic acid (31 mg, 0.18 mmol), 2-methoxy-4-(3-methyl-4-((R)-14(R)-5-oxopyrrolidin-3-yl)ethoxy)-3H-imidazo[4,5-c]pyridin-6-yl)benzonitrile 3B.14 was synthesized.

Workup

  1. customwas synthesized

Sources & evidence

ORD record
ord-7756113a4aaf411688d4b4cc7b824c3e
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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