2,2-Dimethylmorpholine → HCID 67284943, compound

HRID 1618721Notes

Reaction equation

HRID 1618721 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[C:10]([Cl:13])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=1.[CH3:16][C:17]1([CH3:23])[O:22][CH2:21][CH2:20][NH:19][CH2:18]1>CC(O)C>[Cl:13][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][C:8]=2[F:14])[N:3]=[C:2]([N:19]2[CH2:20][CH2:21][O:22][C:17]([CH3:23])([CH3:16])[CH2:18]2)[C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 189596742,2-DimethylmorpholineHCID 596310402,4-Dichloro-5,7-difluoro-3-methylquinoline

Product 1

HCID 67284943HCID 67284943, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

2,4-dichloro-5,7-difluoro-3-methylquinoline (1.0 g, 4.03 mmol) and 2,2-dimethylmorpholine (0.46 mL, 4.03 mmol) were slurried in 2-propanol (10 mL) and heated in a microwave reactor at 120° C. for 5 h. The reaction was then concentrated to dryness and purified by column chromatography (hexanes:EtOAc, 1:0 to 1:1) to give 4-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)-2,2-dimethylmorpholine. 1H NMR (400 MHz, chloroform-d) δ ppm 7.31 (1H, ddd, J=9.7, 2.7, 1.5 Hz), 6.89 (1H, ddd, J=12.3, 8.9, 2.5 Hz), 3.93-3.98 (2H, m), 3.23-3.28 (2H, m), 3.10 (2H, s), 2.47 (3H, s), 1.37 (6H, s). Mass Spectrum (ESI) m/e=327.2 (M+1).

Workup

  1. concentrationThe reaction was then concentrated to dryness
  2. custompurified by column chromatography (hexanes:EtOAc, 1:0 to 1:1)

Sources & evidence

ORD record
ord-0797210f9ec1408899fcde33bff7be23
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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