Morpholine → HCID 69217042, compound

HRID 272726Notes

Reaction equation

HRID 272726 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[C:5]([N+:21]([O-:23])=[O:22])[CH:4]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>C1(C)C=CC=CC=1>[Cl:20][C:18]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:4][C:5]=2[N+:21]([O-:23])=[O:22])[CH:19]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 69219616HCID 69219616, compound

Product 1

HCID 69217042HCID 69217042, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of Example 570A (80 mg, 0.2 mmol) and morpholine (35 mg, 0.4 mmol) in 4 mL of toluene was heated under reflux for two hours. After the reaction mixture was cooled to room temperature, it was loaded onto silica gel for purification that yielded 76 mg of the desired product (94%). MS (DCI) m/e 406 (M+H)+; 1H NMR (300 MHz, DMSO-d6) □ 10.61 (s, 1H), 8.04 (d, J=1.87 Hz, 1H), 7.95 (d, J=8.73 Hz, 1H,) 7.65-7.66 (m, 1H), 7.61 (dd, J=8.73, 1.87 Hz, 1H), 7.46 (d, J=1.87 Hz, 1H), 7.10 (dd, J=8.58, 2.03 Hz, 1H), 3.88 (s, 3H), 3.57-3.59 (m, 4H), 3.39 (s, 2H), 2.28-2.90 (m, 4H).

Workup

  1. temperatureunder reflux for two hours
  2. customit was loaded onto silica gel for purification

Sources & evidence

ORD record
ord-6bbd65976d314a1a8b22f72622af780d
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

Loading…