Triethylamine → HCID 178520141, compound

HRID 2289997Notes

Reaction equation

HRID 2289997 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.[Br:35][CH2:36][C:37](Br)=[O:38]>CN(C1C=CN=CC=1)C.CN(C=O)C>[Br:35][CH2:36][C:37]([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]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 178522910HCID 178522910, compound

Product 1

HCID 178520141HCID 178520141, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxypropyl)-3-quinolinecarboxamide from Example 110 (0.23 g), Et3N (0.090 mL), and catalytic DMAP (5-10 mol %) in 20 mL DMF is cooled to 0° C. Bromoacetyl bromide (0.050 mL) is added in one portion. The reaction is stirred at 0° C. for 20 minutes, then at room temperature for 1.5 h. Once the reaction was complete, it is partitioned between CH2Cl2 and H2O. The aqueous layer is extracted 3× with CH2Cl2. The organics are combined, dried over Na2SO4, filtered, and concentrated under reduced pressure to give a liquid which subsequently crystallizes to an off-white solid when it is dried on the vacuum pump overnight. The solid is triturated in CH2Cl2 /hexanes, filtered, and dried to give the desired product (0.27 g, 0.53 mmol, 91%).

Workup

  1. waitat room temperature for 1.5 h
  2. customit is partitioned between CH2Cl2 and H2O
  3. extractionThe aqueous layer is extracted 3× with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a liquid which
  8. customsubsequently crystallizes to an off-white solid when it
  9. customis dried on the vacuum
  10. waitpump overnight
  11. customThe solid is triturated in CH2Cl2 /hexanes
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-53e89759afaf4017af831e00cf82ca31
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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