Water → HCID 57486791, compound

HRID 577781

Reaction equation

HRID 577781 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]([F:46])([F:45])[C:9]1[CH:10]=[C:11]([CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:40]=1)[CH2:12][NH:13][CH2:14][C:15]1[C:16]([N:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)[CH2:27][CH2:26]2)=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2.Cl[C:48]([O:50][CH2:51][CH3:52])=[O:49].O>C1COCC1>[CH2:51]([O:50][C:48](=[O:49])[N:13]([CH2:12][C:11]1[CH:38]=[C:39]([C:41]([F:44])([F:42])[F:43])[CH:40]=[C:9]([C:8]([F:7])([F:45])[F:46])[CH:10]=1)[CH2:14][C:15]1[C:16]([N:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]3)[CH2:27][CH2:26]2)=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:52]

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 57486818(3,5-Bis-trifluoromethyl-benzyl)-[2-(4-cyclohexylmethyl-piperazin-1-yl)-quinolin-3-ylmethyl]-amine

Product 1

HCID 57486791HCID 57486791, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Anhydrous potassium carbonate (0.17 g, 1.23 mmol) was added to a solution of (3,5-bis-trifluoromethyl-benzyl)-[2-(4-cyclohexylmethyl-piperazin-1-yl)-quinolin-3-yl-methyl]-amine (0.23 g, 0.4 mmol) in anhydrous THF (5 mL). After stirring 0.5 h, ethyl chloroformate (0.06 mL, 0.6 mmol) was added slowly under a nitrogen atmosphere. After stirring at RT for overnight, water (25 mL) was added, and the mixture was extracted with ethyl acetate (3×25 mL). The combined organic phases were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a colorless liquid. Purification by silica gel chromatography and eluting with 10-30% ethyl acetate/hexane afforded the desired final product as a viscous liquid (0.206 g), yield: 81%.

Workup

  1. stirringAfter stirring at RT for overnight
  2. extractionthe mixture was extracted with ethyl acetate (3×25 mL)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a colorless liquid
  8. customPurification by silica gel chromatography
  9. washeluting with 10-30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-6c6d9fba56754af1b0b8c2794cd47fd3
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Linked notes

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