Tetrahydrofuran → 4-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(3-hydroxypropyl)-amine

HRID 132008노트

반응식

HRID 132008 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH:15][CH2:16][CH2:17][C:18]#N)=[N:12][O:13][N:14]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1C[O:29]CC1>>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH:15][CH2:16][CH2:17][CH2:18][OH:29])=[N:12][O:13][N:14]=1

참가 물질

4

반응물 3

HCID 8028Tetrahydrofuran2회HCID 21226445Aluminium lithium hydrideHCID 1363893133-[4-(1H-Benzoimidazol-2-yl)-furazan-3-ylamino]-propionitrile

생성물 1

HCID 1364137544-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(3-hydroxypropyl)-amine

실험 절차

A solution of 4-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(2-cyanoethyl)-amine (0.272 g, 0.947 mmol, Example 6a) in THF (5 ml) is added dropwise at 0° C. to an efficiently stirred suspension of LiAlH4 (0.054 g, 1.42 mmol) in THF (5 ml). After stirring for 16 hours at room temperature the mixture is quenched by careful addition of aqueous saturated solution of sodium sulphate. The suspension is filtered and the filtrate evaporated to dryness. Crystallization by addition of hexane yields the title compound in pure form. 1H-NMR (400 MHz, d6-DMSO): 13.6 (s, 1H); 7.66 (m, 2H); 7.31 (m, 2H); 6.92 (t, 1H); 4.61 (m, 1H); 3.51 (m, 2H); 3.39 (m, 2H); 1.81 (m, 2H).

후처리

  1. customis quenched by careful addition of aqueous saturated solution of sodium sulphate
  2. filtrationThe suspension is filtered
  3. customthe filtrate evaporated to dryness
  4. customCrystallization
  5. additionby addition of hexane

출처 및 근거

ORD 기록
ord-de7ab902035242448b14cd187f63707b
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07385061B2

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