Morpholine → 5-Bromo-6-morpholino-N-(4-(trifluoromethoxy)phenyl)nicotinamide

HRID 525666Notes

Reaction equation

HRID 525666 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[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>>[Br:1][C:2]1[C:3]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][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 8083MorpholineHCID 867025955-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 899067015-Bromo-6-morpholino-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Stage 6.1 using 5-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 6.2) and morpholine to afford an off-white solid. UPLC-MS (Condition 3) tR=1.20 min, m/z=445.9 [M+H]+, m/z=443.9 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 3.37-3.46 (m, 4H) 3.69-3.81 (m, 4H) 7.39 (d, J=8.78 Hz, 2H) 7.86 (d, J=9.16 Hz, 2H) 8.47 (d, J=2.13 Hz, 1H) 8.80 (d, J=2.13 Hz, 1H) 10.44 (s, 1H).

Workup

  1. customto afford an off-white solid

Sources & evidence

ORD record
ord-3ee36540bc40404fbdc5a08e9457e43a
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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