تفاعل #84053

ord-70027d3c3d4d42b3bc9f47f06148eaaa

معادلة التفاعل

Nc1ccc2ncccc2c1
6-aminoquinoline
Cl.O=C(CC1CN2CCC1CC2)Oc1c(F)c(F)c(F)c(F)c1F
pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride
CN(C)C=O
DMF
Cl
hydrochloric acid
O=C([O-])[O-]
carbonate
Cl.O=C(CC1CN2CCC1CC2)Nc1ccc2cccnc2c1
title compound
Cl.O=C(CC1CN2CCC1CC2)Nc1ccc2cccnc2c1
2-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(7-quinolinyl)acetamide hydrochloride

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.WAITAfter 1 h
  2. 2
    ترشيحthe polystyrene resin is filtered off
  3. 3
    غسيلwashed with THF
  4. 4
    تركيزThe combined filtrates are concentrated in vacuo
  5. 5
    أخرىthe crude product is purified by preparative HPLC
  6. 6
    أخرىThe hydrochloride is prepared
  7. 7
    workup.ADDITIONby mixing the product
  8. 8
    تركيزconcentrating again
  9. 9
    أخرىDrying under high vacuum

الإجراء التجريبي

90.3 mg (0.24 mmol) of pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride are dissolved in 1 ml of DMF, mixed with 51.6 mg (0.36 mmol) of 6-aminoquinoline and stirred at room temperature overnight. 1 g of MP-carbonate (polymer-bound carbonate, capacity: 2.5-3.5 mmol/g; from Argonaut Technologies, USA) is added. After 1 h, the polystyrene resin is filtered off and washed with THF. The combined filtrates are concentrated in vacuo, and the crude product is purified by preparative HPLC. The hydrochloride is prepared by mixing the product with a mixture of 1 M hydrochloric acid and acetonitrile and concentrating again. Drying under high vacuum results in 44 mg (50.2% of theory) of the title compound.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09433614B2uspto-grants-2016_09