Sodium hydride → HCID 21101943, compound

HRID 1353336Notes

Reaction equation

HRID 1353336 reaction equation
[C:1]([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])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31][NH2:32]>>[C:1]([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:32][CH2:31][CH2:30][N:29]([CH3:33])[CH3:28])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 66053N,N-DimethylethylenediamineHCID 21101706HCID 21101706, compound

Product 1

HCID 21101943HCID 21101943, compoundYield 56.5%

Procedure

4-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-7-chloroquinol-2-one (145 mg, 0.4 mmol), sodium hydride (15 mg, 0.6 mmol), N-phenyl(trifluoromethylsulfon)imide (202 mg, 0.56 mmol), and N,N-dimethylethylenediamine (276 μL, 2.4 mmol) are treated according to method E yielding 98 mg of 4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-7-chloro-2-[2-(dimethylamino)ethylamino]quinoline. 38 mg thereof are treated with TFA-CH2Cl2 1:1 (0.6 mL) for 1 h and concentrated. The residue is converted into the title product with 4-fluorophenyl isocyanate (16 μL) and triethylamine (120 μL).

Sources & evidence

ORD record
ord-a628fafebdf34cb991936716e485db5e
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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