Hydrochloric Acid → 2-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)acetic acid

HRID 1775550Notes

Reaction equation

HRID 1775550 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][C:8]([O-:10])=[O:9])[N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[C:17]#[C:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Na+].[N:26]([O-])=O.[Na+].[ClH:30]>C(OCC)C.O>[Cl:30][C:17]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:26][N:1]=[C:2]2[N:6]([CH2:7][C:8]([OH:10])=[O:9])[N:5]=[C:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:3]=12

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 70982572sodium 2-(5-amino-3-phenyl-4-(phenylethynyl)-1H-pyrazol-1-yl)acetate

Product 1

HCID 665757822-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A suspension of sodium 2-(5-amino-3-phenyl-4-(phenylethynyl)-1H-pyrazol-1-yl)acetate (2 g, 6.0 mmol) in diethylether (10 mL) and concentrated HCl (50 mL) was cooled at −15° C. before sodium nitrite (0.62 g, 8.0 mmol) in water (5 mL) was added dropwise. The solution was allowed to warm up to room temperature and left stirring for further 18 h. The reaction mixture was carefully quenched with an aqueous solution of Na2CO3 at 10° C., until pH basic, and then extracted EtOAc, backwashed with water then brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was purified using chromatography (silica gel, gradient 2 to 10% diethylether/CH2Cl2) yielding Compound 47 as a yellow foam (580 mg).

Workup

  1. additionwas added dropwise
  2. waitleft
  3. customThe reaction mixture was carefully quenched with an aqueous solution of Na2CO3 at 10° C.
  4. dry with materialbrine, dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified

Sources & evidence

ORD record
ord-91d5e2090b5843c382407a9dd8e28efe
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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