Chlorosuccinimide → HCID 86665223, compound

HRID 409943Notes

Reaction equation

HRID 409943 reaction equation
[F:1][CH:2]([F:28])[C:3]1[CH:7]=[C:6]([CH:8]([F:10])[F:9])[N:5]([CH2:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[S:21][CH:22]=[C:23]([CH:25]=[N:26][OH:27])[N:24]=3)[CH2:16][CH2:15]2)=[O:13])[N:4]=1.[CH:29]([C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:33][CH:32]=1)=[CH2:30].C(=O)([O-])O.[K+].ClN1C(=O)CCC1=O>C(OCC)(=O)C.O>[F:28][CH:2]([F:1])[C:3]1[CH:7]=[C:6]([CH:8]([F:9])[F:10])[N:5]([CH2:11][C:12]([N:14]2[CH2:15][CH2:16][CH:17]([C:20]3[S:21][CH:22]=[C:23]([C:25]4[CH2:30][CH:29]([C:31]5[CH:32]=[CH:33][C:34]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:35][CH:36]=5)[O:27][N:26]=4)[N:24]=3)[CH2:18][CH2:19]2)=[O:13])[N:4]=1

Participants

8

Reactant 4

HCID 31398ChlorosuccinimideHCID 516893Potassium BicarbonateHCID 11736129tert-butyl (4-ethenylphenyl)carbamateHCID 866652212-(1-{[3,5-Bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carbaldehyde oxime

Product 1

HCID 86665223HCID 86665223, compound

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carbaldehyde oxime (1.50 g) and tert-butyl (4-vinylphenyl)carbamate (0.94 g) in ethyl acetate (140 ml) were added, at room temperature, potassium hydrogencarbonate (1.79 g) and N-chlorosuccinimide (0.50 g), and then one drop of water. After the reaction mixture had been stirred at 60° C. for 3 h, ethyl acetate and water were added, and the mixture was extracted with ethyl acetate. The organic extracts were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave tert-butyl (4-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-O-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl)carbamate (0.90 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic extracts were dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-09e02d909f9f469c83c007bea9173278
Source dataset
uspto-grants-2014_06
Patent number
US08759527B2

Reaction notes

Loading…