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

HRID 517784Notes

Reaction equation

HRID 517784 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.[C:32](Cl)(=[O:34])[CH3:33].O>C(Cl)Cl>[C:32]([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:34])[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 666545664-[5-(1-piperazinylmethyl)-1H-tetrazol-1-yl]-2-(trifluoromethyl)benzonitrile

Product 1

HCID 666564964-{5-[(4-acetyl-1-piperazinyl)methyl]-1H-tetrazol-1-yl}-2-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[5-(1-piperazinylmethyl)-1H-tetrazol-1-yl]-2-(trifluoromethyl)benzonitrile (Example 101, 67 mg, 0.199 mmol) in DCM (2 mL) was added triethylamine (55 μL, 0.395 mmol) and then acetyl chloride (21 μL, 0.295 mmol). The reaction mixture was stirred at room temperature for 30 minutes under argon atmosphere. Water (2 mL) was added, and the mixture poured onto a hydrophobic cartridge. The heavier organic phase was concentrated under vacuum to leave white crystals. Purification by MDAP left a white solid, 4-{5-[(4-acetyl-1-piperazinyl)methyl]-1H-tetrazol-1-yl}-2-(trifluoromethyl)benzonitrile (48 mg).

Workup

  1. additionthe mixture poured onto a hydrophobic cartridge
  2. concentrationThe heavier organic phase was concentrated under vacuum
  3. customto leave white crystals
  4. customPurification by MDAP
  5. waitleft a white solid, 4-{5-[(4-acetyl-1-piperazinyl)methyl]-1H-tetrazol-1-yl}-2-(trifluoromethyl)benzonitrile (48 mg)

Sources & evidence

ORD record
ord-025652ef523b430a94e682221056c746
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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