(3S)-pyrrolidin-3-ol → (S)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

HRID 73809

Reaction equation

HRID 73809 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[NH:23]1[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24]1>>[Br:1][C:2]1[C:3]([N:23]2[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8]

Participants

3

Reactant 2

HCID 2733874(3S)-pyrrolidin-3-olHCID 867025955-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 86702636(S)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Stage 8.1 using 5-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 2.3) and (S)-pyrrolidin-3-ol to afford an off-white crystalline powder. HPLC (Condition 4) tR=5.83 min, UPLC-MS (Condition 3) tR=1.06 min, m/z=446.1 [M+H]+.

Workup

  1. customto afford an off-white crystalline powder

Sources & evidence

ORD record
ord-7f8fe8431301407aa3b316be3ef96699
Source dataset
uspto-grants-2014_09
Patent number
US08829195B2

Linked notes

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