Lithium borohydride → N-(3-chloro-4-fluorophenyl)-4-(3-hydroxypropyl)-1,2,5-oxadiazole-3-carboxamide

HRID 1845759Notes

Reaction equation

HRID 1845759 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:13]([CH2:17][CH2:18][C:19](OCC)=[O:20])=[N:14][O:15][N:16]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Li+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:13]([CH2:17][CH2:18][CH2:19][OH:20])=[N:14][O:15][N:16]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 58941764Ethyl 3-(4-[(3-chloro-4-fluorophenyl)amino]carbonyl-1,2,5-oxadiazol-3-yl)propanoate

Product 1

HCID 58941800N-(3-chloro-4-fluorophenyl)-4-(3-hydroxypropyl)-1,2,5-oxadiazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(4-[(3-chloro-4-fluorophenyl)amino]carbonyl-1,2,5-oxadiazol-3-yl)propanoate (97.5 mg, 0.285 mmol) in THF (1.2 mL) was added lithium tetrahydroborate (14.3 mg, 0.656 mmol) at 0° C. under an atmosphere of nitrogen. The reaction solution was allowed to warm to rt for 2 h. The reaction was quenched with MeOH and concentrated. The residue was purified by flash chromatography (60% ethyl acetate/hexane) to give product. LCMS for C12H12ClFN3O3(M+H)+: m/z=300.1.

Workup

  1. customThe reaction was quenched with MeOH
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography (60% ethyl acetate/hexane)
  4. customto give product

Sources & evidence

ORD record
ord-c20c366039244ce29e5bf2ced4648858
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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