4-[(4-Fluorophenyl)ethynyl]benzoic acid → N-[(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)methyl]-4-[(4-fluorophenyl)ethynyl]-N-hexylbenzamide

HRID 551941Notes

Reaction equation

HRID 551941 reaction equation
[CH2:1]([NH:7][CH2:8][C:9]1[CH:21]=[CH:20][C:12]2[O:13][C:14]([CH3:19])([CH3:18])[O:15][C:16](=[O:17])[C:11]=2[CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]#[C:30][C:31]2[CH:39]=[CH:38][C:34]([C:35]([OH:37])=O)=[CH:33][CH:32]=2)=[CH:25][CH:24]=1>>[CH3:19][C:14]1([CH3:18])[O:13][C:12]2[CH:20]=[CH:21][C:9]([CH2:8][N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:35](=[O:37])[C:34]3[CH:33]=[CH:32][C:31]([C:30]#[C:29][C:26]4[CH:25]=[CH:24][C:23]([F:22])=[CH:28][CH:27]=4)=[CH:39][CH:38]=3)=[CH:10][C:11]=2[C:16](=[O:17])[O:15]1

Participants

3

Reactant 2

HCID 226288574-[(4-Fluorophenyl)ethynyl]benzoic acidHCID 575545526-[(hexylamino)methyl]-2,2-dimethyl-4H-1,3-benzodioxin-4-one

Product 1

HCID 57554481N-[(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)methyl]-4-[(4-fluorophenyl)ethynyl]-N-hexylbenzamideYield 98.5%

Procedure

The title compound was prepared following procedure described in example 20, step e) from 6-[(hexylamino)methyl]-2,2-dimethyl-4H-1,3-benzodioxin-4-one (490 mg, 1.68 mmol) and 4-[(4-fluorophenyl)ethynyl]benzoic acid (484 mg, 2.02 mmol). Purification of the crude product by flash chromatography on silicagel (EtOAc/c-Hex (20/80) gave 850 mg (98%) of the title compound. HPLC, Rt: 5.54 min (purity: 99.9%). LC/MS, M+(ESI): 514.1. 1H NMR (CDCl3) δ: 7.45-7.90 (m, 6H), 7.37 (d, J=8.1 Hz, 2H), 7.00 (t, J=8.8 Hz, 2H), 6.94 (d, J=8.5 Hz, 1H), 4.69 (s, 1.5H), 4.45 (s, 0.5H), 3.39 (s, 0.5H), 3.14 (s, 1.5H), 1.07-1.77 (m, 14H), 0.80 (m, 3H).

Workup

  1. customThe title compound was prepared following procedure
  2. customPurification of the crude product by flash chromatography on silicagel (EtOAc/c-Hex (20/80)

Sources & evidence

ORD record
ord-893c97b5076a46dc9d4041a9bf5b1b07
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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