Triethylamine → HCID 23537689, compound

HRID 1792552Notes

Reaction equation

HRID 1792552 reaction equation
[N:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[C:18]([C:41]([F:44])([F:43])[F:42])=[N:19][N:20]([C:22]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH:21]=4)[CH:15]=3)[N:10]=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[N:52]1([C:58](Cl)=[O:59])[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1.C(OCC)(=O)C>ClCCl.O>[O:55]1[CH2:56][CH2:57][N:52]([C:58]([N:4]2[CH2:5][CH2:6][N:1]([C:7]3[C:16]4[C:11](=[CH:12][CH:13]=[C:14]([C:17]5[C:18]([C:41]([F:43])([F:42])[F:44])=[N:19][N:20]([C:22]([C:23]6[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=6)([C:35]6[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=6)[C:29]6[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=6)[CH:21]=5)[CH:15]=4)[N:10]=[CH:9][CH:8]=3)[CH2:2][CH2:3]2)=[O:59])[CH2:53][CH2:54]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 848104-Morpholinecarbonyl chlorideHCID 22031274HCID 22031274, compound

Product 1

HCID 23537689HCID 23537689, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

While a solution of 118 mg 4-piperazin-1-yl-6-[3-(trifluoromethyl)-1-trityl-1H-4-pyrazolyl]quinoline obtained in Example 188 and 61 mg triethylamine in dichloromethane was stirred under ice-cooling in a stream of nitrogen, 35 μL 4-morpholine carbonyl chloride was added thereto, and the mixture was stirred overnight at room temperature. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 125 mg of the title compound as a colorless amorphous.

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5227e25de751439ba43db5c57969150f
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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