p-Fluorophenethylamine → HCID 21101940, compound

HRID 1353350Notes

Reaction equation

C([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[NH:17][C:16](=O)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.[H-].[Na+].[F:28][C:29]1[CH:37]=[CH:36][C:32]([CH2:33][CH2:34][NH2:35])=[CH:31][CH:30]=1>>[CH2:23]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=3)[N:17]=[C:16]([NH:35][CH2:34][CH2:33][C:32]3[CH:36]=[CH:37][C:29]([F:28])=[CH:30][CH:31]=3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])[CH2:14][CH2:15][CH3:16]

Participants

Reactant 3

HCID 4653p-Fluorophenethylamine

HCID 24758Sodium hydride

HCID 21101706HCID 21101706, compound

Product 1

HCID 21101940HCID 21101940, compound

Procedure

4-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-7-chloroquinol-2-one (150 mg, 0.41 mmol), sodium hydride (15 mg, 0.6 mmol), N-phenyl(trifluoromethylsulfon)imide (208 mg, 0.58 mmol), and 4-fluorophenethylamine (0.22 mL, 1.65 mmol) are treated according to method E yielding 4-[4-(butoxycarbonyl)piperazin-1-yl]-7-chloro-2-[2-(4-fluorophenyl)ethylamino]quinoline, which is deprotected with TFA in CH2Cl2 and transformed into the title product according to method C using 4-fluorophenyl isocyanate (18 μL, 0.16 mmol) and triethylamine (110 μL, 0.79 mmol) to give a colorless solid.

Sources & evidence

ORD record: ord-e8adc4381ae14ecab7c31b37df3109b8
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220856B2

Reaction notes

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