Ethanolamine → 7-Chloro-3-[4-(2-hydroxyethylcarbamoyl)-benzyl]-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester

HRID 1697073Notes

Reaction equation

HRID 1697073 reaction equation
[CH3:1][O:2][C:3]([C:5]1N(C2C=CC=CC=2)[C:7]2[C:12]([C:13](=[O:25])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([OH:24])=O)=[CH:18][CH:17]=1)=[CH:11][CH:10]=[C:9]([Cl:26])[CH:8]=2)=[O:4].[NH2:33][CH2:34][CH2:35][OH:36].[CH:37]1[CH:38]=[CH:39][C:40]2[N:45](O)N=N[C:41]=2[CH:42]=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:45]([C:40]2[CH:39]=[CH:38][CH:37]=[CH:42][CH:41]=2)[C:7]2[C:12]([C:13](=[O:25])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:24])[NH:33][CH2:34][CH2:35][OH:36])=[CH:18][CH:17]=1)=[CH:11][CH:10]=[C:9]([Cl:26])[CH:8]=2)=[O:4]

Participants

8

Reactant 5

HCID 700EthanolamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 251817183-(4-Carboxybenzyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl ester

Product 1

HCID 251043037-Chloro-3-[4-(2-hydroxyethylcarbamoyl)-benzyl]-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl esterYield 54.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(4-carboxybenzyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl ester (167 mg, 0.37 mmol), 2-aminoethanol (34 mg, 0.56 mmol), HOBt (50 mg), EDCI (142 mg, 0.74 mmol) and DIPEA (0.5 mL) in DCM (10 mL) and DMF (0.4 mL) was stirred at RT for 2 h. The reaction mixture was then partitioned between water and EtOAc. The organic layer was separated, washed twice with water, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified twice by flash chromatography to afford 7-chloro-3-[4-(2-hydroxyethylcarbamoyl)-benzyl]-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (99 mg) as an off-white powder. MS=491 [M+H]+; MP=162-163.5° C.

Workup

  1. customThe reaction mixture was then partitioned between water and EtOAc
  2. customThe organic layer was separated
  3. washwashed twice with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified twice by flash chromatography

Sources & evidence

ORD record
ord-dc4fe49c454b4382864ee52f6f4a8258
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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