Sodium Carbonate → HCID 178504750, compound

HRID 719858Notes

Reaction equation

HRID 719858 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[C:13]([NH:15][C:16]2[CH:21]=[CH: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:30].[NH2:31][OH:32].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[Cl:30][C:6]1[CH:5]=[C:4]([C@@H:12]([CH2:24][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22](=[NH:23])[NH:31][OH:32])=[CH:18][N:17]=2)=[O:14])[CH:3]=[CH:2][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 67483081HCID 67483081, compound

Product 1

HCID 178504750HCID 178504750, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-N-(5-cyano-pyridin-2-yl)-3-cyclopentyl-propionamide (74 mg, 0.17 mmol) in ethanol (1 mL) and water (0.5 mL) was treated with hydroxylamine hydrochloride (14 mg, 0.21 mmol) and sodium carbonate (9 mg, 0.08 mmol). This solution was then heated at 70° C. for 1.5 h, after which time, the product precipitated out of solution. The resulting solid was collected by filtration, washed with water, and dried under vacuum to afford 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(N-hydroxycarbamimidoyl)-pyridin-2-yl]-propionamide (27 mg, 34%) as a white solid: (ES)+-HRMS m/e calcd for C21H25ClN4O4S (M+H)+ 465.1358, found 465.1362.

Workup

  1. customafter which time, the product precipitated out of solution
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-96ec52a6ab9c41868e150f631efa1088
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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