Methanol → HCID 22909026, compound

HRID 1379026Notes

Reaction equation

HRID 1379026 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.C(N([CH2:28][CH3:29])CC)C.[C:30](OC(=O)C)(=[O:32])[CH3:31].C[OH:38]>ClCCl>[C:30]([N:12]1[C:11]2=[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:9][N:10]2[CH2:15][CH2:14][N:13]1[C:28](=[O:38])[CH3:29])(=[O:32])[CH3:31]

Participants

6

Reactant 4

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 135554955HCID 135554955, compound

Product 1

HCID 22909026HCID 22909026, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 7-(4-fluorophenyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (148 mg) and triethylamine (101 mg) in dry dichloromethane was added acetic anhydride (54 mg). The reaction mixture was stirred at ambient temperature for 4 hours and then, to the mixture was added methanol (1 ml). After standing for 30 minutes, the mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel. The first fraction was concentrated in vacuo and the obtained oil was crystallized from a mixture of diethyl ether and n-hexane to give 1,2-diacetyl-7-(4-fluorophenyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo-[5,1-c][1,2,4]triazine (22 mg).

Workup

  1. waitAfter standing for 30 minutes
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel
  4. concentrationThe first fraction was concentrated in vacuo
  5. customthe obtained oil was crystallized from a mixture of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-fd5c70f85be847e6a6f0f97a985b6e40
Source dataset
uspto-grants-1997_09
Patent number
US05670503

Reaction notes

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