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3-(Trifluoromethyl)benzaldehyde → 5-[1-(3-Trifluoromethyl-benzyl)-piperidin-4-ylamino]-[1,3,4]thiadiazole-2-carbonitrile

HRID 1426386
Notes
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Reaction equation

HRID 1426386 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[S:12][C:11]([C:13]#[N:14])=[N:10][N:9]=2)[CH2:3][CH2:2]1.[F:15][C:16]([F:26])([F:25])[C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C)C=O.C(OCC)(=O)C>[F:15][C:16]([F:25])([F:26])[C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8]2[S:12][C:11]([C:13]#[N:14])=[N:10][N:9]=2)[CH2:5][CH2:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 679903-(Trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 593235735-(Piperidin-4-ylamino)-[1,3,4]thiadiazole-2-carbonitrile

Product 1

HCID 250549455-[1-(3-Trifluoromethyl-benzyl)-piperidin-4-ylamino]-[1,3,4]thiadiazole-2-carbonitrileYield 9%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-(piperidin-4-ylamino)-[1,3,4]thiadiazole-2-carbonitrile (D6) (0.16 g, 0.76 mmol), 3-(trifluoromethyl)benzaldehyde (0.152 ml, 1.14 mmol) and sodium triacetoxyborohydride (0.24 g, 0.95 mmol) in N,N-dimethylformamide (3 ml) was stirred at room temperature for 16 h. After this period, the reaction mixture was diluted with ethyl acetate and extracted with a saturated solution of sodium carbonate (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; 1-4% ammonia in methanol (7M)/dichloromethane) to yield E17 (0.025 g, 9%) as a white solid. C16H16F3N5S requires 367. Found 368 (MH+).

Workup

  1. waitAfter this period
  2. extractionextracted with a saturated solution of sodium carbonate (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; 1-4% ammonia in methanol (7M)/dichloromethane)

Sources & evidence

ORD record
ord-b8e4d45a06dc43cf81db0b3a8a6f7756
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08933101B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes