(2,4-Dimethoxypyrimidin-5-yl)boronic acid → 1-Cyclohexyl-2-[2-[2-(2,4-dimethoxypyrimidin-5-yl)-5-methoxy-phenyl]-6-quinolyl]benzimidazole-5-carboxylic acid

HRID 1788546Notes

Reaction equation

HRID 1788546 reaction equation
ClC1C=C(C=CC=1F)[C:5]1[C:10]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:21]4[N:25]([CH:26]5[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]5)[C:24]5[CH:32]=[CH:33][C:34]([C:36]([OH:38])=[O:37])=[CH:35][C:23]=5[N:22]=4)[CH:17]=3)[N:12]=2)=[CH:9][C:8]([O:39][CH3:40])=[CH:7][CH:6]=1.COC(C1C=CC2N(C3CCCCC3)C(C3C=C4C(=CC=3)N=C(C3C=C(OC)C=CC=3Br)C=C4)=NC=2C=1)=O.[CH3:83][O:84][C:85]1[N:90]=[C:89]([O:91][CH3:92])[C:88](B(O)O)=[CH:87][N:86]=1>>[CH:26]1([N:25]2[C:24]3[CH:32]=[CH:33][C:34]([C:36]([OH:38])=[O:37])=[CH:35][C:23]=3[N:22]=[C:21]2[C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][CH:15]=2)[N:12]=[C:11]([C:10]2[CH:9]=[C:8]([O:39][CH3:40])[CH:7]=[CH:6][C:5]=2[C:88]2[C:89]([O:91][CH3:92])=[N:90][C:85]([O:84][CH3:83])=[N:86][CH:87]=2)[CH:20]=[CH:19]3)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

4

Reactant 3

HCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 5275992HCID 5275992, compoundHCID 68922215HCID 68922215, compound

Product 1

HCID 52761031-Cyclohexyl-2-[2-[2-(2,4-dimethoxypyrimidin-5-yl)-5-methoxy-phenyl]-6-quinolyl]benzimidazole-5-carboxylic acidYield 7%

Procedure

Following the full procedure and workup for Compound 366, Compound 365b (100 mg, 0.175 mmol) was reacted with 2,4-dimethoxypyrimidine-5-boronic acid (34 mg, 0.2625 mmol) to produce the title compound (8 mg, 7% yield).

Sources & evidence

ORD record
ord-39fad7e43001435c9baa4847ee94145c
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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