Dicyclohexylcarbodiimide → 4-[[(3-Chloro-4-methoxyphenyl)methyl]amino]-6-cyano-3-quinolinecarboxylic acid pentafluorophenyl ester

HRID 1368921Notes

Reaction equation

HRID 1368921 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]#[N:23])[CH:20]=3)[N:15]=[CH:14][C:13]=2[C:24]([OH:26])=[O:25])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[F:27][C:28]1[C:33](O)=[C:32]([F:35])[C:31]([F:36])=[C:30]([F:37])[C:29]=1[F:38].C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C.C(OCC)(=O)C>[F:27][C:28]1[C:33]([O:25][C:24]([C:13]2[CH:14]=[N:15][C:16]3[C:21]([C:12]=2[NH:11][CH2:10][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=2)=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=3)=[O:26])=[C:32]([F:35])[C:31]([F:36])=[C:30]([F:37])[C:29]=1[F:38]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 12069380HCID 12069380, compound

Product 1

HCID 120693834-[[(3-Chloro-4-methoxyphenyl)methyl]amino]-6-cyano-3-quinolinecarboxylic acid pentafluorophenyl esterYield 41%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 275 mg (0.748 mmol) of 4-[[(3-chloro-4-methoxyphenyl)-methyl]amino]-6-cyano-3-quinolinecarboxylic acid was added 276 mg (1.50 mmol, 2.0 eq) pentafluorophenol, and the mixture was dispersed in 5 mL anhydrous DMF under nitrogen. To this dispersion was added a solution of 231 mg (1.12 mmol, 1.5 eq) of dicyclohexylcarbodiimide (Aldrich) in 2 mL anhydrous ethyl acetate at RT. The resulting mixture was stirred for 18 hours. The reaction was then diluted with 10 mL EtAc, and the white precipitate was filtered and discarded. The filtrate was concentrated in vacuo, and the residue was triturated with 5% MeOH/95% CH 2Cl2 to give 164 mg (0.307 mmol, 41% yield) of the title compound as a white solid: LC/MS: M/Z 534 (M+H) observed, 100% purity; mp: decomposed 215-217° C. LC: 4.15.

Workup

  1. additionThe reaction was then diluted with 10 mL EtAc
  2. filtrationthe white precipitate was filtered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was triturated with 5% MeOH/95% CH 2Cl2

Sources & evidence

ORD record
ord-3a6de525bfaa475ab0703b4d006c8412
Source dataset
uspto-grants-2003_06
Patent number
US06576644B2

Reaction notes

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