تفاعل #216685

ord-b2418bde8f3a4cce8e8df936eeb8a109

معادلة التفاعل

Cc1ccccc1
toluene
Nc1sc2c(c1C(=O)c1ccccc1Cl)CCN(C(=O)C1CC1)C2
2-amino-3-(2-chlorobenzoyl)-6-cyclopropanecarbonyl-4,5,6,7-tetrahydro-thieno [2,3-C]pyridine
O=C([O-])O.[Na+]
sodium hydrogencarbonate
CC(Br)C(=O)Br
2-bromopropionyl bromide
O=C([O-])O.[Na+]
sodium hydrogencarbonate
CC(Br)C(=O)Br
2-bromopropionyl bromide
CC(Br)C(=O)Nc1sc2c(c1C(=O)c1ccccc1Cl)CCN(C(=O)C1CC1)C2
intended compound
CC(Br)C(=O)Nc1sc2c(c1C(=O)c1ccccc1Cl)CCN(C(=O)C1CC1)C2
2-(2-Bromopropionylamino)-3-(2-chlorobenzoyl)-6-cyclopropanecarbonyl-4,5,6,7-tetrahydrothieno[2,3-C]pyridine

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONwas added
  2. 2
    درجة الحرارةwhile heating to 50° to 60° C
  3. 3
    أخرىthe reaction
  4. 4
    workup.ADDITIONwas added
  5. 5
    غسيلthe reaction solution was washed once with a saturated saline solution
  6. 6
    تجفيفdried with anhydrous magnesium sulfate
  7. 7
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure

الإجراء التجريبي

450 ml of toluene and 150 ml of water were added to 21.83 g of 2-amino-3-(2-chlorobenzoyl)-6-cyclopropanecarbonyl-4,5,6,7-tetrahydro-thieno [2,3-C]pyridine. 10.16 g of sodium hydrogencarbonate was further added, to which 9.5 ml of 2-bromopropionyl bromide was added while heating to 50° to 60° C. Moreover, a sodium hydrogencarbonate aqueous solution (10.6 g of sodium hydrogencarbonate and 150 ml of water1) and 5 ml of 2-bromopropionyl bromide were added to complete the reaction. After the completion of the reaction, ethyl acetate was added and the reaction solution was washed once with a saturated saline solution and dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 29.9 g of the intended compound (at a quantitative yield).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05468740uspto-grants-1995_11