Pyridine → HCID 68467281, compound

HRID 503007Notes

Reaction equation

HRID 503007 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1([C:11]2[N:15]3[CH2:16][CH2:17][NH:18][CH2:19][CH2:20][C:14]3=[N:13][N:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1.N1C=CC=CC=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>ClCCl>[C:27]([N:18]1[CH2:19][CH2:20][C:14]2=[N:13][N:12]=[C:11]([C:6]3([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[CH2:7][CH2:8][CH2:9][CH2:10]3)[N:15]2[CH2:16][CH2:17]1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 68465849HCID 68465849, compound

Product 1

HCID 68467281HCID 68467281, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[1-(2-Thienyl)cyclopentyl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-d][1,4]diazepine (190 mg) was dissolved in dichloromethane (15 ml) and then pyridine (106 μl) and acetic anhydride (62 μl) were added at room temperature, followed by stirring at the same temperature for 15 hours. The residue obtained by removing the solvent by evaporation was diluted with ethyl acetate and washed with 0.3M hydrochloric acid, water, and brine, successively. The solution was dried over anhydrous magnesium sulfate and filtered and then the solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=99:1 to 95:5) to obtain 110 mg of 7-acetyl-3-[1-(2-thienyl)cyclopentyl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-d][1,4]diazepine (white solid).

Workup

  1. customThe residue obtained
  2. customby removing the solvent
  3. customby evaporation
  4. additionwas diluted with ethyl acetate
  5. washwashed with 0.3M hydrochloric acid, water, and brine
  6. dry with materialThe solution was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed by evaporation under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (chloroform:methanol=99:1 to 95:5)

Sources & evidence

ORD record
ord-88a80b905dcb4cde891073b8a4718aae
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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