Morpholine → HCID 22051155, compound

HRID 1832044Notes

Reaction equation

HRID 1832044 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=2[F:16])[C:5]([CH:17]=O)=[CH:4][C:3]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[F:28].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>ClCCl>[Br:1][C:2]1[C:7](=[O:8])[N:6]([C:9]2[C:10]([F:16])=[CH:11][CH:12]=[CH:13][C:14]=2[F:15])[C:5]([CH2:17][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[CH:4][C:3]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[F:28]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 22050819HCID 22050819, compound

Product 1

HCID 22051155HCID 22051155, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by reacting 5-bromo-4-[(2,4-difluorobenzyl)oxy]-1-(2,6-difluorophenyl)-6-oxo-1,6-dihydropyridine-2-carbaldehyde (0.456 g, 1 mmol) with morpholine (0.13 ml, 1.5 mmol) and triacetoxy sodium borohydride (0.42 g, 2.0 mmol) in dichloromethane (7 mL) by using a similar procedure to the one described for Example 468. The crude product was purified by flash column chromatography. Elution with (50:50→0:100) hexanes-ethyl acetate to give 0.15 g (29% yield) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 7.75-7.57 (m, 2H), 7.43-7.31 (m, 3H), 7.20 (dt, J=8.64, 2.48 Hz, 2H), 6.85 (s, 1H), 5.44 (s, 2H), 3.37 (app t, J=4.37 Hz, 4H), 3.13 (s, 2H), 2.08 (t, J=4.19 Hz, 4H); ES-HRMS m/z 527.0600 (M+H calcd for C23H20BrF4N2O3 requires 527.0594).

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified by flash column chromatography
  3. washElution with (50:50→0:100) hexanes-ethyl acetate

Sources & evidence

ORD record
ord-21554671e90f4dffa4ccb6a403105402
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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