1,3-Dichloroacetone → HCID 57888998, compound

HRID 1820212Notes

Reaction equation

HRID 1820212 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:26])[CH2:13][CH2:12][N:11]([C:14](=[O:23])[C@H:15]([NH:19][C:20]([NH2:22])=[S:21])[CH:16]([CH3:18])[CH3:17])[CH2:10][C:9]2([CH3:25])[CH3:24])=[CH:4][CH:3]=1.[Cl:27][CH2:28][C:29](=O)[CH2:30]Cl>CC(C)=O>[Cl:27][CH2:28][C:29]1[N:22]=[C:20]([NH:19][C@H:15]([CH:16]([CH3:17])[CH3:18])[C:14]([N:11]2[CH2:12][CH2:13][C@@:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)([OH:26])[C:9]([CH3:24])([CH3:25])[CH2:10]2)=[O:23])[S:21][CH:30]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 57889035HCID 57889035, compound

Product 1

HCID 57888998HCID 57888998, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 1-((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)thiourea (29 mg, 0.073 mmol) in acetone (300 μL) was added 1,3-dichloropropan-2-one (14 mg, 0.105 mmol) and the reaction mixture was stirred overnight at rt. The solvents were removed and the residue purified via column chromatography (SiO2, 25% EtOAc/hep then 50% EtOAc/hep then 10% EtOAc with 0.06% DIPEA). (R)-2-(4-(chloromethyl)thiazol-2-ylamino)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methylbutan-1-one (35 mg, >95% yield) was isolated as a clear glass. HPLC purity: >99%, rt 3.87 min; MS found: 470.22 (M+)+.

Workup

  1. customThe solvents were removed
  2. customthe residue purified via column chromatography (SiO2, 25% EtOAc/hep

Sources & evidence

ORD record
ord-dddc656dbd4541be9b0688c521c02545
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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