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Potassium Carbonate → HCID 135520522, compound

HRID 1437634
Notes
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Reaction equation

HRID 1437634 reaction equation
Cl.[F:2][C:3]([F:29])([F:28])[C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:37][C:38]1[NH:39][C:40](=[O:43])[NH:41][N:42]=1>CN(C=O)C.O>[F:29][C:3]([F:2])([F:28])[C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:23]=1)[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][N:12]([CH2:37][C:38]2[NH:39][C:40](=[O:43])[NH:41][N:42]=2)[CH2:11][C@H:10]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 86606807cis-4-[[3,5-Bis(trifluoromethyl)benzyl]oxy]-3-phenylpiperidine hydrochlorideHCID 1355466853H-1,2,4-Triazol-3-one, 5-(chloromethyl)-1,2-dihydro-

Product 1

HCID 135520522HCID 135520522, compoundYield 29.3%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
2×
HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixed solution of the compound (0.15 g) obtained in Example 1 and potassium carbonate (0.047 g) in DMF (2 ml) and water (0.02 ml), 5-(chloromethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (0.046 g) synthesized by the method described in the document (e.g., Tetrahedron Letters, Vol. 41, pages 8661-8664) was added at 0° C., and the reaction mixture was stirred at 0° C. for 3 hours. The reaction mixture was poured into water, and then the product was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried, and then the solvent was evaporated under reduced pressure. The obtained residue was isolated and purified by silica gel column chromatography (ethyl acetate:methanol=20:1) to obtain the title compound as colorless crystals (0.050 g, 29%).

Workup

  1. additionwas added at 0° C.
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was isolated
  7. custompurified by silica gel column chromatography (ethyl acetate:methanol=20:1)

Sources & evidence

ORD record
ord-16a1ab4a394a4bbb9e0f9fbed14c83a9
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07622487B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes