Acetone → HCID 178440305, compound

HRID 1930061Notes

Reaction equation

HRID 1930061 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH:26]2[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]2)[S:12][C:13]=1[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([CH:23]([CH3:25])[CH3:24])=[N:21][N:22]=2)[N:19]=1.[BH4-].[Na+].CC(C)=O>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([C@H:26]2[CH2:31][CH2:30][C@H:29]([OH:32])[CH2:28][CH2:27]2)[S:12][C:13]=1[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([CH:23]([CH3:25])[CH3:24])=[N:21][N:22]=2)[N:19]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 579298484-(4-(2,4-Difluorophenyl)-5-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)thiazol-2-yl)cyclohexanone

Product 1

HCID 178440305HCID 178440305, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-5 °C

Procedure

The 4-(4-(2,4-difluorophenyl)-5-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)thiazol-2-yl)cyclohexanone (0.495 g, 1.09 mmol) was dissolved in MeOH (5 mL) then cooled to about −5° C. Sodium borohydride (0.041 g, 1.09 mmol) was added and the mixture was stirred for about 5 min. Acetone was added, the solvents were concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel with DCM/MeOH (95:5) as an eluent then by RP-HPLC (Table 1, Method f) to give the title compound (0.209 g, 42%): LC/MS (Table 1, Method a) Rt=2.29 min; MS m/z: 456.2 (M+H)+.

Workup

  1. concentrationthe solvents were concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel with DCM/MeOH (95:5) as an eluent

Sources & evidence

ORD record
ord-b4fc40ae3c664ce48692e360a941f848
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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