Morpholine → HCID 25254220, compound

HRID 219447Notes

Reaction equation

HRID 219447 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[C:10]([O:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[C:9]([O:22][CH3:23])[C:8]([Cl:24])=[C:7]([CH3:25])[C:6]=1[C:26](=[O:28])[CH3:27].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>>[Cl:24][C:8]1[C:7]([CH3:25])=[C:6]([C:26](=[O:28])[CH3:27])[C:5]([O:4][CH2:3][CH2:2][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[C:10]([O:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:9]=1[O:22][CH3:23]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 59583480HCID 59583480, compound

Product 1

HCID 25254220HCID 25254220, compoundYield 26%

Procedure

Example 1e (83 mg, 0.18 mmol) was reacted with morpholine (3 mL) as described under General Procedure G and the crude mixture was purified by flash chromatography (silica-gel, DCM/EtOAc/MeOH 1:0:0, 9:8:2) to afford the title compound (23 mg, 26%) as light creamy oil. 1H NMR (300 MHz, CDCl3) δ 7.20-7.13 (m, 2H), 6.99-6.93 (m, 2H), 4.10-4.03 (m, 4H), 3.86 (s, 3H), 3.68 (t, J=4.4 Hz, 4H), 2.78 (t, J=7.6 Hz, 2H), 2.62 (t, J=5.5 Hz, 2H), 2.51 (s, 3H), 2.46 (t, J=4.45 Hz, 4H), 2.18 (s, 3H), 2.07-1.98 (m, 2H). MS (ES+) m/z 479.9 (M+H+).

Workup

  1. customthe crude mixture was purified by flash chromatography (silica-gel, DCM/EtOAc/MeOH 1:0:0, 9:8:2)

Sources & evidence

ORD record
ord-a08727d1494f45b48852729f13dbe471
Source dataset
uspto-grants-2012_06
Patent number
US08202513B2

Reaction notes

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