Trifluoroacetic acid → HCID 25182112, compound

HRID 1697078Notes

Reaction equation

HRID 1697078 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[CH3:8][O:9][C:10]([C:12]1[N:13]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:14]2[C:19]([C:20](=[O:45])[C:21]=1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([N:32]3[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]3)(=[O:31])=[O:30])=[CH:25][CH:24]=1)=[CH:18][CH:17]=[C:16]([Cl:46])[CH:15]=2)=[O:11]>C(Cl)Cl>[F:4][C:3]([F:6])([F:5])[C:1]([OH:7])=[O:2].[CH3:8][O:9][C:10]([C:12]1[N:13]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:14]2[C:19]([C:20](=[O:45])[C:21]=1[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)(=[O:31])=[O:30])=[CH:27][CH:28]=1)=[CH:18][CH:17]=[C:16]([Cl:46])[CH:15]=2)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59846263HCID 59846263, compound

Product 1

HCID 25182112HCID 25182112, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of TFA and DCM (1:4, 5 mL) was added to 3-[4-(4-t-butoxycarbonylpiperazine-1-sulfonyl)-benzyl]-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl ester (48 mg, 0.07 mmol) and the resulting mixture stirred at RT for 2 h. The reaction mixture was evaporated under reduced pressure, and the oily solid residue was purified by flash chromatography (DCM/MeOH, 100:0 to 90:10) to afford 7-chloro-4-oxo-1-phenyl-3-[4-(piperazine-1-sulfonyl)-benzyl]-1,4-dihydro-quinoline-2-carboxylic acid methyl ester trifluoroacetate as an off-white powder. MS=552 [M+H]+; MP=203.0-205.0° C.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customthe oily solid residue was purified by flash chromatography (DCM/MeOH, 100:0 to 90:10)

Sources & evidence

ORD record
ord-ca8f23f4bb6b4b22977b6ac5d8c0892b
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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