Dimethylformamide → 4-[(3-benzyloxy-4-methoxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

HRID 1685662

반응식

HRID 1685662 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=1)[CH2:12][N:13]([C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=1)[N:14]1[CH:18]=[N:17][N:16]=[CH:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C(C1C=CC(NN2C=NN=C2)=CC=1)#N.CN([CH:49]=[O:50])C>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][C:29]=1[O:50][CH3:49])[CH2:12][N:13]([C:19]1[CH:20]=[CH:21][C:22]([C:25]#[N:26])=[CH:23][CH:24]=1)[N:14]1[CH:15]=[N:16][N:17]=[CH:18]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 10307909Benzonitrile, 4-(4H-1,2,4-triazol-4-ylamino)-HCID 219768914-[(3-benzyloxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

생성물 1

HCID 167478434-[(3-benzyloxy-4-methoxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole수율 44%

실험 절차

The title compound was prepared by adapting the method for 4-[(3-benzyloxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole using NaH (60% dispersion in oil, 0.22 g, 5.4 mmol), 4-[(4-cyanophenyl)amino]-4H-[1,2,4]triazole (1.0 g, 5.68 mmol) and 4-methoxy-3-benzyloxybenzyl bromide[Meyers, 1989] (1.66 g, 5.4 mmol) in anhydrous DMF (5 mL) to give 4-[(3-benzyloxy-4-methoxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole as an off-white solid (0.97 g, 44%) after recrystallisation; mp. 138-141° C.; δH (400 MHz, CDCl3) 3.89 (s, 3H), 4.72 (s, 2H), 5.12 (s, 2H), 6.59 (AA′BB′, 2H), 6.62 (d, J=2, 1H), 6.64 (dd, J=7.8, 2, 1H), 6.79 (d, J=7.8, 1H), 7.28-7.34 (m, 5H), 7.57 (AA′BB′, 2H), 7.74 (s, 2H); LRMS (FAB+) m/z (rel. intensity) 412 (100, [M+H]), 343 (51), 227 (72%); HPLC: tR=2.21 min (94%); HRMS (FAB+): Found 412.1774 C24H22N5O2 requires 412.1776.

후처리

  1. customThe title compound was prepared

출처 및 근거

ORD 기록
ord-80573cf542fa44209ac4cbebc23afbf6
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148415B2

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