Methyl chloroglyoxylate → HCID 59846170, compound

HRID 1697096Notes

Reaction equation

HRID 1697096 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:21])[CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][CH2:12]2)=[C:4]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:39][O:40][C:41](=[O:45])[C:42](Cl)=O>C1COCC1>[CH3:39][O:40][C:41]([C:42]1[N:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:4]2[C:5]([C:8](=[O:21])[C:9]=1[CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([S:17]([CH3:20])(=[O:18])=[O:19])[CH2:13][CH2:12]1)=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[O:45]

Participants

5

Reactant 3

HCID 79846Methyl chloroglyoxylateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 66815843HCID 66815843, compound

Product 1

HCID 59846170HCID 59846170, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 1-(4-fluoro-2-phenylamino-phenyl)-3-(4-methanesulfonyl-piperidin-1-yl)-propan-1-one (500 mg) in THF (8 mL) under N2 was added NaHMDS (3.1 mL, 1 M in THF). After 5 min, chloro-oxoacetic acid methyl ester (0.28 mL) was added, and the mixture stirred for 2 h at 0° C., then for 1 h at RT. The reaction mixture was quenched with NH4Cl (sat'd aq), extracted with EtOAc, and chromatographed (0-20% MeOH/DCM) to provide 7-fluoro-3-(4-methanesulfonyl-piperidin-1-ylmethyl)-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (301 mg, Compound 126). M+H=473; mp=190.0-191.0° C.

Workup

  1. waitfor 1 h at RT
  2. customThe reaction mixture was quenched with NH4Cl (sat'd aq)
  3. extractionextracted with EtOAc
  4. customchromatographed (0-20% MeOH/DCM)

Sources & evidence

ORD record
ord-8255e65c6edb463393790c8a26281359
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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