Diisopropylethylamine → Methyl 5-[{4-[(4-butylphenyl)ethynyl]benzoyl}(hexyl)amino]-2-fluorobenzoate

HRID 551983Notes

Reaction equation

[F:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:19]([C:23]1[CH:28]=[CH:27][C:26]([C:29]#[C:30][C:31]2[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=2)=[CH:25][CH:24]=1)[CH2:20][CH2:21][CH3:22].CCN(C(C)C)C(C)C>C1COCC1.CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:19]([C:23]1[CH:28]=[CH:27][C:26]([C:29]#[C:30][C:31]2[CH:39]=[CH:38][C:34]([C:35]([N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:9]3[CH:10]=[CH:11][C:2]([F:1])=[C:3]([CH:8]=3)[C:4]([O:6][CH3:7])=[O:5])=[O:36])=[CH:33][CH:32]=2)=[CH:25][CH:24]=1)[CH2:20][CH2:21][CH3:22]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 2-fluoro-5-(hexylamino)benzoate (185 mg; 0.73 mmol) in THF (15 mL) were added 4-[(4-butylphenyl)ethynyl]benzoyl chloride (260 mg; 0.88 mmol), DIEA (0.15 mL; 0.88 mmol) and DMAP (20 mg). The mixture was stirred at 60° C. under N2 atmosphere for 1 hour. It was then diluted with DCM (100 mL), washed with HCl 0.1N (50 mL) and a saturated solution of NaHCO3 (100 mL). The organic layer was dried over magnesium sulfate, filtrated and the solvent was removed under reduced pressure to give 480 mg of a brown solid. Purification by flash chromatography on silicagel (c-Hex/EtOAc, 90:10) gave 170 mg (45.3%) of the title compound as a white solid. HPLC, Rt: 6.14 min (purity=99.5%). LC/MS: M+(ESI): 514.3.

Workup

washwashed with HCl 0.1N (50 mL)
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltrated
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-42a0a95a04cf404086c5ec72d37817c0
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947851B2

Reaction notes

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