Methyl 3-mercaptopropionate → HCID 15981315, compound

HRID 1836442Notes

Reaction equation

HRID 1836442 reaction equation
Cl[C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[SH:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22].CC(C)([O-])C.[K+]>C1COCC1>[CH3:24][O:23][C:21](=[O:22])[CH2:20][CH2:19][S:18][C:2]1[CH:17]=[CH:16][C:5]([C:6](=[O:7])[NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 18050Methyl 3-mercaptopropionateHCID 2653166HCID 2653166, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15981315HCID 15981315, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-N-(4-fluoro-phenyl)-nicotinamide (0.25 g, 1.0 mmol) in 3 mL of THF was added methyl 3-mercaptopropionate (0.16 mL, 1.5 mmol) then potassium tert-butoxide (0.22 g, 2.0 mmol). The mixture was stirred for 3 h then poured into ice water and the solids washed with water and collected. Purification by trituration using ethyl acetate gave 13 mg (4%) of the titled product as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 10.33 (s, 1H), 8.94 (m,1H), 8.09 (m, 1H), 7.74 (m, 2H), 7.43 (m, 1H), 7.17 (m, 2H), 3.59 (s, 3H), 3.37 (m, 2H), 2.75 (m, 2H); MS (EI) m/z 333.10 (M−H)−.

Workup

  1. washthe solids washed with water
  2. customcollected
  3. customPurification by trituration

Sources & evidence

ORD record
ord-c6333323857e49b991d29e344b87c80f
Source dataset
uspto-grants-2004_08
Patent number
US06777432B1

Reaction notes

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