Hexanal → HCID 57554565, compound

HRID 551971Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:21][C:22]1[CH:23]=[CH:24][C:25]([F:32])=[C:26]([CH:31]=1)[C:27]([O:29][CH3:30])=[O:28].[CH:33](=O)[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][C:16]([CH2:17][N:21]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:22]3[CH:23]=[CH:24][C:25]([F:32])=[C:26]([CH:31]=3)[C:27]([O:29][CH3:30])=[O:28])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 6184Hexanal

HCID 15621043Methyl 5-amino-2-fluorobenzoate

HCID 860770684-[(4-Tert-butylphenyl) ethynyl]benzaldehyde

Product 1

HCID 57554565HCID 57554565, compoundYield 46.1%

Procedure

The title compound was prepared following procedure described in Example 49, step a) from 4-[(4-tert-butylphenyl) ethynyl]benzaldehyde (500 mg; 1.91 mmol, intermediate which may be prepared according to methods disclosed in EP0310378.0.7) and methyl 5-amino-2-fluorobenzoate (322 mg; 1.91 mmol) and hexanal (Aldrich, 690 μl; 5.72 mmol). Purification of the crude (700 mg) by preparative HPLC using a X-Terra column afforded 440 mg (46%) of the title compound as a red oil. HPLC, Rt: 6.46 min (purity=89.9%). LC/MS: M+(ESI): 500.3. 1H NMR (CDCl3) δ: 7.57 (d, J=1.9 Hz, 2H), 7.54 (d, J=2.3 Hz, 2H), 7.45 (d, J=8.3 Hz, 2H), 7.35-7.20 (m, 3H), 7.04 (t, J=9.6 Hz, 1H), 6.85 (m, 1H), 4.61 (s, 2H), 4.00 (s, 3H), 3.47 (t, J=7.72 Hz, 2H), 1.70 (m, 2H), 1.39 (s, 15H), 0.99 (t, J=6.6Hz, 3H).

Workup

customThe title compound was prepared following procedure
customPurification of the crude (700 mg) by preparative HPLC

Sources & evidence

ORD record: ord-5d19a723071d43d88945c7debb5ebdf9
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947851B2

Reaction notes

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