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

HRID 553345Notes

Reaction equation

HRID 553345 reaction equation
[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

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 1363893133-[4-(1H-Benzoimidazol-2-yl)-furazan-3-ylamino]-propionitrile

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-dde274e722b0409d87706d81630193ab
Source dataset
uspto-grants-2011_11
Patent number
USRE042890E1

Reaction notes

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