Acetone → HCID 57520675, compound

HRID 1528109Notes

Reaction equation

HRID 1528109 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[NH:12][C:13]([NH:15][C:16]1[N:21]=[C:20]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:19]=[CH:18][CH:17]=1)=[O:14].[BH4-].[Na+].Cl.C(Cl)Cl.CO.[CH3:36][C:37]([CH3:39])=O>>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[NH:12][C:13]([NH:15][C:16]1[N:21]=[C:20]([CH:22]2[CH2:23][CH2:24][N:25]([CH:37]([CH3:39])[CH3:36])[CH2:26][CH2:27]2)[CH:19]=[CH:18][CH:17]=1)=[O:14]

Participants

6

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 21226129Dichloromethane methanolHCID 57520575HCID 57520575, compound

Product 1

HCID 57520675HCID 57520675, compound

Procedure

To a solution of 50 mg of 1-(8-fluoro-quinolin-4-yl)-3-(1′,2′,3′,4′,5′,6′-hexahydro-[2,4′]bipyridinyl-6-yl)-urea (example 62) (0.137 mmol) in 50 ml of acetone were added 26 mg of sodium borohydride (0.684 mmol) in small portions. The reaction was slightly exotherm. After stirring the reaction mixture over night a small amount of 2M HCl was added to the reaction mixture up to a pH of 3 to destroy the excess of sodium borohydride. After neutralization with sodium bicarbonate, acetone was evaporated under reduced pressure, water added to the residue, the reaction mixture extracted three times with DCM, the organic phases combined and dried over sodium sulfate and the solvent evaporated under reduced pressure. 45 mg of the desired product were obtained as off white powder (yield: 81%) after column chromatography (silica gel, DCM/MeOH 98/2).

Workup

  1. additionwas added to the reaction mixture up to a pH of 3
  2. customto destroy the excess of sodium borohydride
  3. customAfter neutralization with sodium bicarbonate, acetone was evaporated under reduced pressure, water
  4. additionadded to the residue
  5. extractionthe reaction mixture extracted three times with DCM
  6. dry with materialdried over sodium sulfate
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-c35d5080cc6d4311ab37a5a7fd1c0fb4
Source dataset
uspto-grants-2015_07
Patent number
US09090592B2

Reaction notes

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