Pyrrolidine → 5-(4-Chloro-3-methyl-phenyl)-N-((R)-1-hydroxymethyl-3-methyl-butyl)-6-pyrrolidin-1-yl-nicotinamide

HRID 1159313Notes

Reaction equation

CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[C:7](Cl)=[N:6][CH:5]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.[Cl:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[CH3:25].[NH2:29][C@@H:30]([CH2:35][OH:36])[CH2:31][CH:32]([CH3:34])[CH3:33]>>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C:8]2[C:7]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[N:6][CH:5]=[C:4]([CH:9]=2)[C:3]([NH:29][C@@H:30]([CH2:35][OH:36])[CH2:31][CH:32]([CH3:34])[CH3:33])=[O:12])=[CH:23][C:24]=1[CH3:25]

Participants

Reactant 4

HCID 31268Pyrrolidine

HCID 2724002D(-)-Leucinol

HCID 2764313Methyl 5-bromo-6-chloronicotinate

HCID 38546103-Chloro-4-methylphenylboronic acid

Product 1

HCID 248569905-(4-Chloro-3-methyl-phenyl)-N-((R)-1-hydroxymethyl-3-methyl-butyl)-6-pyrrolidin-1-yl-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 43, using 5-bromo-6-chloro-nicotinic acid methyl ester, pyrrolidine (commercially available), 3-chloro-4-methylphenyl-boronic acid (commercially available) and (R)-(−)-leucinol (commercially available) as starting materials. MS (ISP): 416.4 (M+H+).

Workup

customdescribed for the preparation of Example 43

Sources & evidence

ORD record: ord-b0679149d59e4ca8b4ecd9b27f708483
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812028B2

Reaction notes

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