Cyclopropanecarboxaldehyde → Methyl 5-[(4-[(4-butylphenyl)ethynyl]benzyl) (cyclopropylmethyl)amino]-2-fluorobenzoate

HRID 551962

Reaction equation

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

Participants

Reactant 2

HCID 123114Cyclopropanecarboxaldehyde

HCID 11452740Methyl 5-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2-fluorobenzoate

Product 1

HCID 57554559Methyl 5-[(4-[(4-butylphenyl)ethynyl]benzyl) (cyclopropylmethyl)amino]-2-fluorobenzoateYield 54.6%

Procedure

The title compound was prepared following procedure described in example 23, step b) from methyl 5-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2-fluorobenzoate (326 mg; 0.78 mmol) and cyclopropanecarboxaldehyde (Aldrich, 87.94 μl; 1.18 mmol). Purification of the crude by preparative HPLC using a X-Terra column gave 200 mg (54%) of the title compound as a beige oil. HPLC, Rt: 5.91 min (purity: 99.7%), LC/MS, M+(ESI): 470.4, 1H NMR (CDCl3) δ: 7.66 (m, 1H), 7.39 (d, J=7.9 Hz, 4H), 7.00-7.17 (m, 6H), 4.62 (s, 2H), 3.93 (s, 3H), 3.44 (m, 3H), 2.59 (t, J=7.7 Hz, 2H), 1.57 (m, 2H), 1.31 (m, 2H), 0.90 (t, J=7.2 Hz, 3H), 0.53 (d, J=7.2 Hz, 2H), 0.24 (m, 2H).

Workup

customThe title compound was prepared following procedure
customPurification of the crude by preparative HPLC

Sources & evidence

ORD record: ord-bcd0f4891556468eb30e133a7f17f5a3
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947851B2

Linked notes

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