Lithium borohydride → HCID 90414667, compound

HRID 578841Notes

Reaction equation

HRID 578841 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([CH2:14][N:15]3[CH:19]=[N:18][C:17]([C:20](OC)=[O:21])=[N:16]3)[CH:11]=[N:10][C:9]=2[O:24][CH3:25])[CH:5]=[CH:6][CH:7]=1.[BH4-].[Li+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([CH2:14][N:15]3[CH:19]=[N:18][C:17]([CH2:20][OH:21])=[N:16]3)[CH:11]=[N:10][C:9]=2[O:24][CH3:25])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 90415200HCID 90415200, compound

Product 1

HCID 90414667HCID 90414667, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-((6-(3-chlorophenyl)-5-methoxypyrazin-2-yl)methyl)-1H-1,2,4-triazole-3-carboxylate (Example 127, 77.00 mg, 0.21 mmol), in THF (1 mL) was added lithium borohydride (4.66 mg, 0.21 mmol). The mixture was stirred at room temperature for 3 hr. The mixture was diluted with water and extracted into DCM. The combined extracts were dried (Na2SO4) and concentrated under reduced pressure. Purification (FCC, SiO2, 0-5% DCM/MeOH) afforded the title compound (50 mg; 70%). 1H NMR (400 MHz, CD3OD) δ 8.61 (s, 1H), 8.21 (s, 1H), 8.02 (td, J=1.1, 2.1 Hz, 1H), 8.00-7.92 (m, 1H), 7.45-7.38 (m, 2H), 5.53 (s, 2H), 4.59 (s, 2H), 4.06 (s, 3H). [M+H]=332.15.

Workup

  1. extractionextracted into DCM
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customPurification (FCC, SiO2, 0-5% DCM/MeOH)

Sources & evidence

ORD record
ord-53454e5666ab4ce08a0f3e9c779ccef8
Source dataset
uspto-grants-2015_05
Patent number
US09040692B2

Reaction notes

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