Triethylamine → HCID 178505291, compound

HRID 2289995Notes

Reaction equation

HRID 2289995 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][CH2:22][CH2:23][OH:24])=[CH:15][C:14]=3[F:25])=[O:9])=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>CN(C=O)C.CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:35][S:36]([O:24][CH2:23][CH2:22][CH2:21][C:16]1[CH:17]=[C:18]2[C:13](=[C:14]([F:25])[CH:15]=1)[N:12]=[CH:11][C:10]([C:8]([NH:7][CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:27][CH:26]=1)=[O:9])=[C:19]2[OH:20])(=[O:38])=[O:37]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178522910HCID 178522910, compound

Product 1

HCID 178505291HCID 178505291, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxypropyl)-3-quinolinecarboxamide from Example No. 110 (0.13 g) in 10 mL DMF is added NEt3 (0.05 mL) and a spatula tip of DMAP. Methanesulfonyl chloride (0.030 mL) is added dropwise and the reaction is allowed to stir at room temperature overnight. The reaction is partitioned between EtOAc and H2O. The aqueous layer is extracted 3× with EtOAc. The organics are combined, dried over MgSO4, filtered, and concentrated under reduced pressure to give a yellow liquid. The residue is dissolved in CH2Cl2, adsorbed onto silica and chromatographed on a Biotage Flash 40S column (eluent 1% MeOH:CH2Cl2 (1 L) followed by 3% MeOH:CH2Cl2 (2 L)) to afford the desired product as a white solid which is further purified by recrystallization with CH2Cl2 /hexanes. (0.045 g, 0.097 mmol, 29%).

Workup

  1. customThe reaction is partitioned between EtOAc and H2O
  2. extractionThe aqueous layer is extracted 3× with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow liquid
  7. customchromatographed on a Biotage Flash 40S column (eluent 1% MeOH:CH2Cl2 (1 L) followed by 3% MeOH:CH2Cl2 (2 L))

Sources & evidence

ORD record
ord-805ef0647b6b42deb75365439be934e3
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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