반응 #45482

반응 방정식

N-{4-[4-amino-7-(5-formyl-2-furyl)thieno[3,2-c]pyridin-3-yl]-2-methoxyphenyl}-1-methyl-1H-indole-2-carboxamide

sodium borohydride

→

title compound

수율 3.3%

N-(4-{4-amino-7-[5-(hydroxymethyl)-2-furyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide

수율 3.3%

용매

N,N-dimethylformamide

methanol

반응 조건

후처리

1. 1
   기타The solvent was removed in vacuo
2. 2
   기타the residue was partitioned between dichloromethane (10 mL) and 0.1 N hydrochloric acid (10 mL)
3. 3
   기타The layers were separated
4. 4
   추출the aqueous layer was extracted with dichloromethane (3×10 mL)
5. 5
   건조The combined organic layers were dried over anhydrous magnesium sulfate
6. 6
   기타the solvent was removed in vacuo
7. 7
   기타The residue was purified by preparative RP-HPLC (Rainin C18, 8 mm, 300 Å, 25 cm
8. 8
   workup.WAIT40% acetonitrile—0.1M ammonium acetate isocratic for 5 minutes
9. 9
   workup.WAIT40-100% acetonitrile—0M ammonium acetate over 30 min
10. 10
    기타The acetonitrile was removed in vacuo

실험 절차

A mixture of N-{4-[4-amino-7-(5-formyl-2-furyl)thieno[3,2-c]pyridin-3-yl]-2-methoxyphenyl}-1-methyl-1H-indole-2-carboxamide (0.060 g, 0.12 mmol) and sodium borohydride (0.013 g, 0.344 mmol) in N,N-dimethylformamide (4 mL) and methanol (4 mL) was stirred at ambient temperature for 18 hours. The solvent was removed in vacuo and the residue was partitioned between dichloromethane (10 mL) and 0.1 N hydrochloric acid (10 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (3×10 mL). The combined organic layers were dried over anhydrous magnesium sulfate and the solvent was removed in vacuo. The residue was purified by preparative RP-HPLC (Rainin C18, 8 mm, 300 Å, 25 cm; 40% acetonitrile—0.1M ammonium acetate isocratic for 5 minutes, then 40-100% acetonitrile—0M ammonium acetate over 30 min, 21 ml/min). The acetonitrile was removed in vacuo and the aqueous mixture was lyophilized to give the title compound (2.1 mg, 0.004 mmol) as a white solid.

출처