4-Fluorophenylboronic acid → HCID 11949892, compound

HRID 1766516Notes

Reaction equation

HRID 1766516 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[C:7](Cl)=[N:6][CH:5]=1.Cl.[CH:14]1([CH2:17][NH:18][CH3:19])[CH2:16][CH2:15]1.[F:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.Cl.[NH2:31][CH2:32][C@H:33]1[CH2:38][CH2:37][CH2:36][CH2:35][C@H:34]1[OH:39]>>[CH:14]1([CH2:17][N:18]([CH3:19])[C:7]2[C:8]([C:24]3[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=3)=[CH:9][C:4]([C:3]([NH:31][CH2:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]3[OH:39])=[O:12])=[CH:5][N:6]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 4

HCID 2856454-Fluorophenylboronic acidHCID 2764313Methyl 5-bromo-6-chloronicotinateHCID 12919210(Cyclopropylmethyl)(methyl)amine hydrochlorideHCID 53393211HCID 53393211, compound

Product 1

HCID 11949892HCID 11949892, compound

Procedure

The title compound was synthesized in analogy to Example 74, using 5-bromo-6-chloro-nicotinic acid methyl ester, cyclopropylmethyl methylamine hydrochloride, (4-fluoro-phenyl)-boronic acid and cis-2-aminomethyl-1-cyclohexanol hydrochloride as starting materials to yield racemic 6-(cyclopropylmethyl-methyl-amino)-5-(4-fluoro-phenyl)-N-((1RS,2RS)-2-hydroxy-cyclohexylmethyl)-nicotinamide. MS (ISP) 412.1 (M+H)+.

Workup

  1. customThe title compound was synthesized in analogy to Example 74

Sources & evidence

ORD record
ord-8a6b772282924f5ea15d9413a5fef578
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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