Pyridine → HCID 70110849, compound

HRID 1379036Notes

Reaction equation

HRID 1379036 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:11]3[NH:12][NH:13][CH2:14][CH2:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:29]1([CH2:35][C:36]([Cl:38])=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O>[ClH:38].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:11]3[N:12]([C:36](=[O:37])[CH2:35][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[NH:13][CH2:14][CH2:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7679Phenylacetyl chlorideHCID 135554955HCID 135554955, compound

Product 1

HCID 70110849HCID 70110849, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

To a mixture of 7-(4-fluorophenyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (118 mg) and pyridine (64 mg) in N-methyl-1-pyrrolidone (2 ml) was added phenylacetyl chloride (65 mg) under nitrogen atmosphere with ice cooling. After stirring for 1 hour at 4° C., the reaction mixture was poured into cold water. The separated oil was extracted with ethyl acetate and the extract was washed with brine, dried and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtain oil was dissolved in 10% methanolic hydrogen chloride (1 ml). The resulting clear solution was concentrated in vacuo. The residue was crystallized from ethyl acetate to give 7-(4-fluorophenyl)-2-phenylacetyl-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine hydrochloride (130 mg).

Workup

  1. extractionThe separated oil was extracted with ethyl acetate
  2. washthe extract was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel
  6. dissolutionthe obtain oil was dissolved in 10% methanolic hydrogen chloride (1 ml)
  7. concentrationThe resulting clear solution was concentrated in vacuo
  8. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-832b3cc3273b49f9890a43b149c3f6f1
Source dataset
uspto-grants-1997_09
Patent number
US05670503

Reaction notes

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