Ethanol → HCID 118093612, compound

HRID 1520098Notes

Reaction equation

HRID 1520098 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([CH3:9])[N:6]=[C:5]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][S:18]([NH:21][CH3:22])(=[O:20])=[O:19])=[CH:13][CH:12]=2)[CH:4]=1)#[N:2].O1CCOCC1.CCO.[H][H]>[Pd].C(N(CC)CC)C>[NH2:2][CH2:1][C:3]1[N:8]=[C:7]([CH3:9])[N:6]=[C:5]([O:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][S:18]([NH:21][CH3:22])(=[O:20])=[O:19])=[CH:15][CH:16]=2)[CH:4]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 312751,4-DioxaneHCID 118093605HCID 118093605, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 118093612HCID 118093612, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

Combine palladium (18.54 g, 10% on charcoal), 1-[4-(6-cyano-2-methyl-pyrimidin-4-yl)oxyphenyl]-N-methyl-methanesulfonamide (46.34 g, 141.19 mmol), 1,4-Dioxane (278 mL), EtOH (185 mL), and triethylamine (78.7 mL) in a PARR reactor. Seal the PARR reactor and charge it with hydrogen (400 psi). Shake the reactor at room temperature for 4.5 h. Open the reactor and filter the contents through CELITE®. Collect and evaporate the filtrate to provide the title compound as a yellow solid (23.8 g, 48%). MS (m/z): 323 (M+1). Wash the CELITE® pad with a mixture of 1,4-dioxane/MeOH (6×500 mL); collect the filtrate; and evaporate the solvent to provide a second crop of the title compound as a yellow solid (pinky solid, 48%). MS (m/z): 323 (M+1).

Workup

  1. customSeal the PARR reactor
  2. filtrationfilter the contents through CELITE®
  3. customCollect
  4. customevaporate the filtrate

Sources & evidence

ORD record
ord-aab144cc5b6c45d4b35c9c468fe63835
Source dataset
uspto-grants-2015_07
Patent number
US09073901B2

Reaction notes

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