(R)-3-Pyrrolidinol → (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(perfluoroethoxy)phenyl)nicotinamide

HRID 73777Notes

Reaction equation

HRID 73777 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])=[CH:12][CH:11]=1)=[O:8].[NH:26]1[CH2:30][CH2:29][C@@H:28]([OH:31])[CH2:27]1>>[Br:1][C:2]1[C:3]([N:26]2[CH2:30][CH2:29][C@@H:28]([OH:31])[CH2:27]2)=[N:4][CH:5]=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])=[CH:12][CH:11]=1)=[O:8]

Participants

3

Reactant 2

HCID 2759337(R)-3-PyrrolidinolHCID 867026205-bromo-6-chloro-N-(4-(perfluoroethoxy)phenyl)nicotinamide

Product 1

HCID 86702619(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(perfluoroethoxy)phenyl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Stage 9.2 using 5-bromo-6-chloro-N-(4-(perfluoroethoxy)phenyl)nicotinamide (Stage 19.2) and (R)-pyrrolidin-3-ol to afford an off-white crystalline solid. HPLC (Condition 4) tR=6.01 min, UPLC-MS (Condition 3) tR=1.17 min, m/z=496.2 [M+H]+.

Workup

  1. customto afford an off-white crystalline solid

Sources & evidence

ORD record
ord-e4de4fa26b5043f0836f7bd48ae288e1
Source dataset
uspto-grants-2014_09
Patent number
US08829195B2

Reaction notes

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