1-Pentanol → HCID 135526992, compound

HRID 876085Notes

Reaction equation

HRID 876085 reaction equation
[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[NH:4][CH2:3][CH2:2]2.[NH:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]1[O:19][C:18](S)=[N:17][N:16]=1.C(O)CCCC>C(Cl)(Cl)Cl>[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[N:4]([C:18]1[O:19][C:15]([C:11]3[NH:10][CH:14]=[CH:13][CH:12]=3)=[N:16][N:17]=1)[CH2:3][CH2:2]2

Participants

5

Reactant 3

HCID 62761-PentanolHCID 3984071,4-Diazabicyclo(3.2.2)nonaneHCID 178527952HCID 178527952, compound2×

Product 1

HCID 135526992HCID 135526992, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1,4-diazabicyclo[3.2.2]nonane (3.02 g, 23.9 mmol), 5-(1H-pyrrol-2-yl)-1,3,4-oxadiazole-2-thiol (Compound B) (5.0 g, 20.9 mmol) and 1-pentanol (50 ml) was stirred for 15 h. The mixture was solved in chloroform and was filtered through celite. The mixture was purified three times by silica gel chromatography, using chloroform, methanol and aqueous ammonia (89:10:1). The product was dried and evaporated. Yield 382 mg (6%). LC-ESI-HRMS of [M+H]+ shows 260.15096 Da. Calc. 260.15059 Da, dev. 1.4 ppm.

Workup

  1. filtrationwas filtered through celite
  2. customThe mixture was purified three times by silica gel chromatography
  3. customThe product was dried
  4. customevaporated

Sources & evidence

ORD record
ord-d5db2ac124e049269e82353d8f3193b4
Source dataset
uspto-grants-2015_03
Patent number
US08986654B2

Reaction notes

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