Hydrochloric Acid → HCID 15980918, compound

HRID 1836444Notes

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 6-chloro-N-(4-fluoro-phenyl)-nicotinamide (0.20 g, 0.80 mmol) in 10 mL of DMF was added 3-mercaptopropionic acid (0.10 mL, 1.2 mmol) and potassium tert-butoxide (0.31 g, 2.8 mmol) and the mixture heated to 60° C. After 9 h the reaction mixture was poured into ice water, HCl (1 M, aq) added to adjust to pH 6, and the solids removed via filtration. The filtrate was then taken to pH 10 with NaOH (4M, aq) and extracted with ethyl acetate. HCl (6M, aq) was then added to the filtrate to adjust the pH to 4 and extracted with ethyl acetate, dried over sodium sulfate, and the solvents removed in vacuo to yield a white solid. Purification by recrystallization using ethyl acetate gave 0.17 g (66%) of the titled product as a white solid; MS (EI) m/z 319.20 (M−H)−.

Workup

additionadded
customthe solids removed via filtration
extractionextracted with ethyl acetate. HCl (6M, aq)
additionwas then added to the filtrate
extractionextracted with ethyl acetate
dry with materialdried over sodium sulfate
customthe solvents removed in vacuo
customto yield a white solid
customPurification
customby recrystallization

Sources & evidence

ORD record: ord-c04f0eb0c2494affa1d92c47babbf7b3
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777432B1

Reaction notes

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