Triethylamine → 4-(5-{[4-(Propylsulfonyl)-1-piperazinyl]methyl}-1H-tetrazol-1-yl)-2-(trifluoromethyl)benzonitrile

HRID 517788Notes

Reaction equation

HRID 517788 reaction equation
[N:1]1([CH2:7][C:8]2[N:12]([C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([C:21]([F:24])([F:23])[F:22])[CH:14]=3)[N:11]=[N:10][N:9]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:32]([S:35](Cl)(=[O:37])=[O:36])[CH2:33][CH3:34]>C(Cl)Cl>[CH2:32]([S:35]([N:4]1[CH2:3][CH2:2][N:1]([CH2:7][C:8]2[N:12]([C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([C:21]([F:24])([F:22])[F:23])[CH:14]=3)[N:11]=[N:10][N:9]=2)[CH2:6][CH2:5]1)(=[O:37])=[O:36])[CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 666545664-[5-(1-piperazinylmethyl)-1H-tetrazol-1-yl]-2-(trifluoromethyl)benzonitrile

Product 1

HCID 680745154-(5-{[4-(Propylsulfonyl)-1-piperazinyl]methyl}-1H-tetrazol-1-yl)-2-(trifluoromethyl)benzonitrileYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[5-(1-piperazinylmethyl)-1H-tetrazol-1-yl]-2-(trifluoromethyl)benzonitrile (Example 101, 50 mg, 0.15 mmol) was dissolved in DCM and treated with triethylamine (41 μL, 0.29 mmol) followed by 1-propanesulfonyl chloride (20 μL, 0.18 mmol). The mixture was stirred at ambient temperature under argon for 2.5 hours. The reaction mixture was partitioned between water and DCM (5 mL each) and the layers were separated using a hydrophobic frit. The aqueous layer was extracted with further DCM (2×5 mL). The combined DCM extracts were concentrated in vacuo to give the title compound as a pale cream solid (62 mg).

Workup

  1. customThe reaction mixture was partitioned between water and DCM (5 mL each)
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with further DCM (2×5 mL)
  4. concentrationThe combined DCM extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-eab945d9bf304fe69dda1a8515d2bfb6
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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