3,3-Dimethylbutanoyl chloride → HCID 57841359, compound

HRID 733630Notes

Reaction equation

HRID 733630 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].[C:32]([CH2:36][C:37](Cl)=[O:38])([CH3:35])([CH3:34])[CH3:33]>>[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]([C:37](=[O:38])[CH2:36][C:32]([CH3:35])([CH3:34])[CH3:33])[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

3

Reactant 2

HCID 815143,3-Dimethylbutanoyl chlorideHCID 11452740Methyl 5-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2-fluorobenzoate

Product 1

HCID 57841359HCID 57841359, compound

Procedure

The titled compound was prepared following the procedure B using methyl 5-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2-fluorobenzoate and tert-butylacetyl chloride as a pale yellow oil (97%). 1H NMR (CDCl3, 300 MHz) δ 7.61 (dd, J=6.0, 1.9 Hz, 1H), 7.44 (m, 4H), 7.16 (m, 4H), 7.08 (m, 1H), 6.99 (m, 1H), 4.88 (s, 2H), 3.94 (s, 3H), 2.63 (t, J=7.7 Hz, 2H), 2.00 (s, 2H), 1.61 (m, 2H), 1.37 (m, 2H), 0.99 (s, 9H), 0.94 (t, J=7.3 Hz, 3H). M+ (ESI): 514.0, HPLC, Rt: 5.92 min (Purity: 100.0%).

Sources & evidence

ORD record
ord-dcbf06ded78540b5bdb39a3eecbc900e
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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