Sodium Carbonate → HCID 178504739, compound

HRID 2214058Notes

Reaction equation

HRID 2214058 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:12]([CH2:24][CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([C:22]#[N:23])=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[ClH:31].[NH2:32][OH:33].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[Cl:31][C:2]1[CH:3]=[C:4]([CH:12]([CH2:24][CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([C:22](=[NH:23])[NH:32][OH:33])=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 104788602-(3-chloro-4-methanesulfonyl-phenyl)-N-(5-cyano-pyrazin-2-yl)-3-(tetrahydro-pyran-4-yl)-propionamide

Product 1

HCID 178504739HCID 178504739, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-N-(5-cyano-pyrazin-2-yl)-3-(tetrahydro-pyran-4-yl)-propionamide (prepared as in Example 22, 151 mg, 0.34 mmol) in ethanol (2 mL) and water (1 mL) was treated with hydroxylamine hydrochloride (28 mg, 0.40 mmol) and sodium carbonate (35 mg, 0.34 mmol). The reaction was heated at 70° C. for 3 h. At this time, the reaction was concentrated in vacuo and then extracted with 10% methanol/chloroform (3×30 mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 12M, Silica, 20/80 hexanes/ethyl acetate) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-N-[5-(N-hydroxycarbamimidoyl)-pyrazin-2-yl]-3-(tetrahydro-pyran-4-yl)-propionamide (110 mg, 68%) as a white solid: mp 137.2–140.5° C.; (ES)+-HRMS m/e calcd for C20H24ClN5O5S (M+H)+ 482.1260, found 482.1263.

Workup

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. extractionextracted with 10% methanol/chloroform (3×30 mL)
  3. dry with materialThe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae12fe83862c4e0aa75f9078977c2674
Source dataset
uspto-grants-2006_09
Patent number
US07105671B2

Reaction notes

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