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Diisopropylethylamine → [1-(3,4-Difluoro-benzyl)-piperidin-4-yl]-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine

HRID 1426383
Notes
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Reaction equation

HRID 1426383 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[S:9][C:10]([C:13]([F:16])([F:15])[F:14])=[N:11][N:12]=2)[CH2:3][CH2:2]1.[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:21]Br.C(N(C(C)C)CC)(C)C>C(#N)C.ClCCl>[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:21][N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[S:9][C:10]([C:13]([F:16])([F:14])[F:15])=[N:11][N:12]=2)[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 5814364-(Bromomethyl)-1,2-difluorobenzeneHCID 59323569Piperidin-4-yl-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine

Product 1

HCID 25054941[1-(3,4-Difluoro-benzyl)-piperidin-4-yl]-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amineYield 80%

Reagents, catalysts & solvents 2

HCID 6342
Acetonitrile
Solvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of piperidin-4-yl-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine (D4) (0.040 g, 0.16 mmol), 3,4-difluorobenzyl bromide (0.024 ml, 0.19 mmol) and diisopropylethylamine (0.042 ml, 0.24 mmol) in acetonitrile (3 ml) was stirred at 100° C. for 5 min., under microwave irradiation. After cooling to room temperature, the reaction mixture was diluted with dichloromethane and extracted with a 10% solution of ammonium chloride (25 ml). The organic layer was separated, dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; 0-3% ammonia in methanol (7M)/dichloromethane) to yield E5 (0.048 g, 80%) as a solid. C15H15F5N4S requires 378. Found 379 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with a 10% solution of ammonium chloride (25 ml)
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. customthe solvent evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica gel; 0-3% ammonia in methanol (7M)/dichloromethane)

Sources & evidence

ORD record
ord-dca8276863824755988a350dd6f2ab8c
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08933101B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes