Acetic Acid → HCID 178506280, compound

HRID 1674997Notes

Reaction equation

HRID 1674997 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=O)=[N:2]1.[N:12]1([C:18]2[CH:19]=[CH:20][C:21]3[N:22]([C:24]([C:27]([F:30])([F:29])[F:28])=[N:25][N:26]=3)[N:23]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(O)(=O)C>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][N:15]2[CH2:14][CH2:13][N:12]([C:18]3[CH:19]=[CH:20][C:21]4[N:22]([C:24]([C:27]([F:28])([F:29])[F:30])=[N:25][N:26]=4)[N:23]=3)[CH2:17][CH2:16]2)=[N:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14768626-Piperazino-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazineHCID 178520025HCID 178520025, compound

Product 1

HCID 178506280HCID 178506280, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1H-Indazole-3-carboxaldehyde (75 mg, 0.51 mmol) and (polystyrylmethyl)trimethylammonium cyanoborohydride (125 mg, 0.51 mmol) were added to a solution of 6-(piperazin-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (100 mg, 0.37 mmol) in DCM (2 mL)/acetic acid (0.2 mL). The mixture was stirred at ambient temperature for 18 hours. The resin was filtered off and the filtrate was evaporated. The crude product was purified by preparative HPLC (Waters XTerra C18 column, 5μ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% ammonia) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 6-[4-(1H-indazol-3-ylmethyl)piperazin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (89 mg, 60%) as a white solid.

Workup

  1. filtrationThe resin was filtered off
  2. customthe filtrate was evaporated
  3. customThe crude product was purified by preparative HPLC (Waters XTerra C18 column, 5μ silica, 19 mm diameter, 100 mm length)
  4. additionFractions containing the desired compound
  5. customwere evaporated to dryness

Sources & evidence

ORD record
ord-6d76c3141c834d609540ed7122cb1754
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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