Phenethylamine → HCID 11441220, compound

HRID 1785474Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[C:12]3=[CH:13][C:14]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][C:16](=[O:17])[N:11]3[CH2:10][CH2:9]2)[CH:5]=[N:4][CH:3]=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[CH2:76]([NH2:84])[CH2:77][C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1>C1(C)C=CC=CC=1>[CH2:76]([NH:84][C:2]1[N:7]=[C:6]([N:8]2[C:12]3=[CH:13][C:14]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][C:16](=[O:17])[N:11]3[CH2:10][CH2:9]2)[CH:5]=[N:4][CH:3]=1)[CH2:77][C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of 1-(6-chloro-pyrazin-2-yl)-7-phenyl-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-one (85 mg, 0.26 mmol), sodium tert-butoxide (70 mg, 2.8 eq), BINAP (24 mg, 15% eq), and Pd (OAc)2 (9 mg, 15% eq) was added toluene (5 mL) and phenethylamine (39 μL, 1.2 eq). After purged with N2 for 10 min, the overall mixture was heated at 70° C. for 3 h prior to being cooled to room temperature. The resulting material was filtered through Celite and the filtrated cake was washed with DCM/MeOH (98:2) and the filtrates were concentrated. The residual material was purified by a preparative thin-layer chromatography (2% MeOH in DCM) to provide the title compound as a pale yellow solid. MS m/e 410 (M+H)+. Biological Assays

Workup

customAfter purged with N2 for 10 min
temperatureto being cooled to room temperature
filtrationThe resulting material was filtered through Celite
washthe filtrated cake was washed with DCM/MeOH (98:2)
concentrationthe filtrates were concentrated
customThe residual material was purified by a preparative thin-layer chromatography (2% MeOH in DCM)

Sources & evidence

ORD record: ord-ba1c8c7437684ce38dd842cb5b96d860
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504403B2

Reaction notes

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