Sodium borohydride → HCID 51037110, compound

HRID 2039538Notes

Reaction equation

HRID 2039538 reaction equation
[NH2:1][C:2]1[N:14]=[C:13]2[N:4]([C:5]([CH2:17][C:18]3[CH:26]=[CH:25][C:21]4[O:22][CH2:23][O:24][C:20]=4[CH:19]=3)=[N:6][C:7]3[CH:8]=[CH:9][C:10]([C:15]#[N:16])=[CH:11][C:12]=32)[N:3]=1.[BH4-].[Na+]>O1CCCC1.CO.[Co](Cl)Cl>[NH2:16][CH2:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]=[C:5]([CH2:17][C:18]3[CH:26]=[CH:25][C:21]4[O:22][CH2:23][O:24][C:20]=4[CH:19]=3)[N:4]3[N:3]=[C:2]([NH2:1])[N:14]=[C:13]3[C:12]=2[CH:11]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 51036892HCID 51036892, compound

Product 1

HCID 51037110HCID 51037110, compoundYield 14.4%

Reagents, catalysts & solvents 3

HCID 24288Cobalt(II) chlorideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5-benzo[1,3]dioxol-5-ylmethyl-[1,2,4]triazolo[1,5-c]quinazoline-9-carbonitrile (0.07 g, 0.20 mmol), prepared as described in Example 25, in a mixture of tetrahydrofuran (5 mL) and methanol (5 mL), were sequentially added cobalt(II) chloride (0.11 g, 0.81 mmol) and sodium borohydride (0.03 g, 0.81 mmol). The reaction was stirred at room temperature overnight, then the solvent was evaporated. The residue was dissolved in CHCl3/CH3OH 9/1 and washed with ammonium hydroxide solution (pH 12). The organic phase was dried over Na2SO4, filtered and evaporated to obtain a crude which was purified by preparative HPLC to give the title compound (0.01 g, 7% yield).

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in CHCl3/CH3OH 9/1
  3. washwashed with ammonium hydroxide solution (pH 12)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto obtain a crude which
  8. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-f6ac406cc3fb41d18390bfeda29c60c5
Source dataset
uspto-grants-2013_11
Patent number
US08580783B2

Reaction notes

Loading…