(R)-3-Pyrrolidinol → (R)-5-bromo-N-(4-(2-chloro-1,1,2,2-tetrafluoroethyl)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

HRID 924135Notes

Reaction equation

HRID 924135 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:22])([F:21])[C:17]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[NH:25]1[CH2:29][CH2:28][C@@H:27]([OH:30])[CH2:26]1>>[Br:1][C:2]1[C:3]([N:25]2[CH2:29][CH2:28][C@@H:27]([OH:30])[CH2:26]2)=[N:4][CH:5]=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:22])([F:21])[C:17]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8]

Participants

3

Reactant 2

HCID 2759337(R)-3-PyrrolidinolHCID 867026315-bromo-6-chloro-N-(4-(2-chloro-1,1,2,2-tetrafluoroethyl)phenyl)nicotinamide

Product 1

HCID 86702630(R)-5-bromo-N-(4-(2-chloro-1,1,2,2-tetrafluoroethyl)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Stage 171.1 using 5-bromo-6-chloro-N-(4-(2-chloro-1,1,2,2-tetrafluoroethyl)phenyl)nicotinamide (Stage 278.2) and (R)-pyrrolidin-3-ol to afford a white powder. HPLC (Condition 4) tR=6.05 min, UPLC-MS (Condition 3) tR=1.18 min, m/z=498 [M+H]+.

Workup

  1. customto afford a white powder

Sources & evidence

ORD record
ord-ad7e5d51d24040d78124b5018a59970f
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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