Diisopropylethylamine → HCID 71208146, compound

HRID 1887969Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:41])[C:7]([CH2:18][NH:19][C:20](=[O:40])[NH:21][CH:22]3[CH2:27][CH2:26][N:25]([C:28]([O:30]C4C=CC([N+]([O-])=O)=CC=4)=O)[CH2:24][CH2:23]3)=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH3:51][S:52]([CH:55]1[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]1)(=[O:54])=[O:53]>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:41])[C:7]([CH2:18][NH:19][C:20]([NH:21][CH:22]3[CH2:27][CH2:26][N:25]([C:28]([N:58]4[CH2:59][CH2:60][CH:55]([S:52]([CH3:51])(=[O:54])=[O:53])[CH2:56][CH2:57]4)=[O:30])[CH2:24][CH2:23]3)=[O:40])=[CH:8][N:9]2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

In a 20 mL round-bottomed flask, 4-nitrophenyl 4-(3-((7-chloro-4-oxo-1-phenyl-1,4-dihydroquinolin-3-yl)methyl)ureido)piperidine-1-carboxylate (0.100 g, 0.174 mmol), N,N-diisopropylethylamine (112 mg, 152 μL, 0.868 mmol) and 4-(methylsulfonyl)-piperidine (28.3 mg, 0.174 mmol) were combined with DMF (5 mL). The reaction mixture was stirred at 100° C. over the weekend. The reaction mixture was concentrated. The crude product was purified by preparative reverse-phase HPLC, giving the product 1-(7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-3-[1-(4-methanesulfonyl-piperidine-1-carbonyl)-piperidin-4-yl]-urea. MS calcd. for C29H35ClN5O5S [(M+H)+] 600.2, obsd. 600.0.

Workup

concentrationThe reaction mixture was concentrated
customThe crude product was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record: ord-81d5589fe03a4f89b27576485266d599
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501732B2

Reaction notes

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