Triethylamine → HCID 73776183, compound

HRID 1615731Notes

Reaction equation

HRID 1615731 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:13][N:12]=[C:11]2[N:21]([CH2:30][C:31]([OH:33])=[O:32])[N:22]=[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:10]=12.[CH2:34](OC(Cl)=O)[CH:35]([CH3:37])[CH3:36].[BH4-].[Na+]>C1COCC1.Cl>[Cl:8][C:9]1[C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[N:13][N:12]=[C:11]2[N:21]([CH2:30][C:31]([O:33][CH2:34][CH:35]([CH3:37])[CH3:36])=[O:32])[N:22]=[C:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:10]=12

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 665757822-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)acetic acid

Product 1

HCID 73776183HCID 73776183, compoundYield 6.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (535 μL, 3.8 mmol) was added to 2-(4-chloro-3,5-diphenyl-1Hpyrazolo[3,4-c]pyridazin-1-yl)acetic acid (700 mg, 1.92 mmol) in THF (20 mL) at 0° C., followed by the addition of isobutylchloroformate (342 mg, 2.9 mmol). The reaction mixture was stirred for 1 h. Sodium borohydride (220 mg, 5.8 mmol) was then added portionwise and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with 0.5 M HCl and the aqueous layer was extracted twice with ethyl acetate. The combined organic phases were washed with water and brine, dried (phase separator), and concentrated in vacuo. The residue was purified by chromatography (silica gel, ethyl acetate/isohexane 0:1 to 1:0), to provide Compound 12 as a solid (50 mg).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 3 h
  2. extractionthe aqueous layer was extracted twice with ethyl acetate
  3. washThe combined organic phases were washed with water and brine
  4. customdried (phase separator)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (silica gel, ethyl acetate/isohexane 0:1 to 1:0)

Sources & evidence

ORD record
ord-a0ec9875c4fc4eaf83bc768278bbec90
Source dataset
uspto-grants-2014_07
Patent number
US08765762B2

Reaction notes

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