Dimethylamine → HCID 21101948, compound

HRID 1353335Notes

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][NH:29][CH3:30]>>[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]([N:29]([CH3:30])[CH3:28])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 674Dimethylamine

HCID 24758Sodium hydride

HCID 21101706HCID 21101706, compound

Product 1

HCID 21101948HCID 21101948, compoundYield 58.8%

Procedure

4-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-7-chloroquinol-2-one (74 mg, 0.2 mmol), sodium hydride (8 mg, 0.3 mmol), N-phenyl(trifluoromethylsulfon)imide (101 mg, 0.28 mmol), and dimethylamine (2 M in THF, 2 mL, 4.0 mmol) are treated according to method E yielding 46 mg of the 4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-7-chloro-2-dimethylaminoquinoline. This is 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 (19 μL) and triethylamine (0.11 mL).

Sources & evidence

ORD record: ord-94b8ba9a299c439ebcb8fa96f05af34b
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220856B2

Reaction notes

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