تفاعل #7276

ord-47eedb33bf164f6fbd23e37cca184a59

معادلة التفاعل

O=Cc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1
4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde
Nc1cc[nH]n1
3-aminopyrazole
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3
c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2cc[nH]n2)cc1)Cc1nc2ccccc2[nH]1
amine
المردود 23.0%
c1cnc2c(c1)CCCC2N(Cc1ccc(CNc2cc[nH]n2)cc1)Cc1nc2ccccc2[nH]1
(1H-Benzimidazol-2-ylmethyl)-{4-[(1H-pyrazol-3-ylamino)-methyl]-benzyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
المردود 23.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىPurification of the crude material by radial chromatography on silica gel gel (2 mm plate, CH2Cl2/MeOH/NH4OH, 100:1:1

الإجراء التجريبي

Using General Procedure B: To a stirred solution of 4-{[(1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzaldehyde (199 mg, 0.50 mmol) and 3-aminopyrazole (60 mg, 0.72 mmol) in THF (5 mL) and acetic acid (0.2 mL) was added NaBH(OAc)3 (166 mg, 0.78 mmol) and the resultant mixture stirred at room temperature for 2.5 days. Purification of the crude material by radial chromatography on silica gel gel (2 mm plate, CH2Cl2/MeOH/NH4OH, 100:1:1 then 50:1:1) afforded the desired amine (52 mg, 23%) as a white foam.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07084155B2uspto-grants-2006_08