3-fluoro-5-morpholin-4-yl-N-[4-(3-morpholin-4-yl-propenyl)-naphthalen-1-yl]-benzamide → 3-fluoro-5-morpholin-4-yl-N-[4-(3-morpholin-4-yl-propyl)-naphthalen-1-yl]-benzamide

HRID 1641276Notes

Reaction equation

HRID 1641276 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH:29]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]=[CH:19][CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:10][CH:9]=1)=[O:6].[H][H]>[Pd].CO>[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH:29]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH2:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[CH:10][CH:9]=1)=[O:6]

Participants

5

Reactant 2

HCID 667378803-fluoro-5-morpholin-4-yl-N-[4-(3-morpholin-4-yl-propenyl)-naphthalen-1-yl]-benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 595534103-fluoro-5-morpholin-4-yl-N-[4-(3-morpholin-4-yl-propyl)-naphthalen-1-yl]-benzamideYield 46.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-Fluoro-5-morpholin-4-yl-N-[4-(3-morpholin-4-yl-propenyl)-naphthalen-1-yl]-benzamide (56 mg, 117 μmol), is stirred under 1 atmosphere of hydrogen with 10% palladium on carbon (50 mg) in methanol (15 ml) at room temperature for 1 day. Celite° (1 g) is then added and the mixture filtered through a pad of Celite® and washed with methanol (2×10 ml). The filtrate is evaporated to dryness and the purified by column chromatography on silica gel eluted with 5% methanol in ethyl acetate to give 3-fluoro-5-morpholin-4-yl-N-[4-(3-morpholin-4-yl-propyl)-naphthalen-1-yl]-benzamide as a white powder (26 mg). 1H NMR 300 MHz (CDCl3) 8.04(d, 1H, J=11.5 Hz), 7.95(s, 1H), 7.7-7.8(m, 2H), 7.5(m, 2H), 7.35(d, 1H, J=8.6 Hz), 7.3(s, 1H), 7.0(d, 1H, J=10.1 Hz), 6.7 (d, 1H, J=13.0 Hz), 3.8(t, 4H, J=5.7 Hz), 3.7(m, 4H), 3.2(m, 4H), 3.1(t, 2H, J=7.2 Hz), 2.45(s, 6H), 1.9(m, 2H).

Workup

  1. additionCelite° (1 g) is then added
  2. filtrationthe mixture filtered through a pad of Celite®
  3. washwashed with methanol (2×10 ml)
  4. customThe filtrate is evaporated to dryness
  5. customthe purified by column chromatography on silica gel
  6. washeluted with 5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-b15c323718b64ca5839276e11b584a4a
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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