Hydrochloric Acid → (z)-3-[(4-Acetyl-1h-pyrrol-2-yl)methylene]-1,3-dihydro-5-fluoro-4-[(2s,4r)-(4-hydroxy-pyrrolidin-2-yl)ethynyl]-2h-indol-2-one hydrochloride salt

HRID 1069770Notes

Reaction equation

HRID 1069770 reaction equation
[C:1]([C:4]1[CH:5]=[C:6](/[CH:9]=[C:10]2\[C:11](=[O:28])[NH:12][C:13]3[C:18]\2=[C:17]([C:19]#[C:20][C@@H:21]2[CH2:25][C@@H:24]([OH:26])[CH2:23][NH:22]2)[C:16]([F:27])=[CH:15][CH:14]=3)[NH:7][CH:8]=1)(=[O:3])[CH3:2].[ClH:29].C1COCC1.CCCCC>CN(C=O)C.O1CCOCC1>[ClH:29].[C:1]([C:4]1[CH:5]=[C:6](/[CH:9]=[C:10]2\[C:11](=[O:28])[NH:12][C:13]3[C:18]\2=[C:17]([C:19]#[C:20][C@@H:21]2[CH2:25][C@@H:24]([OH:26])[CH2:23][NH:22]2)[C:16]([F:27])=[CH:15][CH:14]=3)[NH:7][CH:8]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8003PentaneHCID 8028TetrahydrofuranHCID 15907928(Z)-3-[(4-Acetyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-5-fluoro-4-[(2S,4R)-(4-hydroxy-pyrrolidin-2-yl)ethynyl]-2H-indol-2-one

Product 1

HCID 69949240(z)-3-[(4-Acetyl-1h-pyrrol-2-yl)methylene]-1,3-dihydro-5-fluoro-4-[(2s,4r)-(4-hydroxy-pyrrolidin-2-yl)ethynyl]-2h-indol-2-one hydrochloride salt

Reagents, catalysts & solvents 1

HCID 217120691,4-dioxane N,N-dimethylformamideSolvent

Procedure

A solution of (Z)-3-[(4-Acetyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-5-fluoro-4-[(2S,4R)-(4-hydroxy-pyrrolidin-2-yl)ethynyl]-2H-indol-2-one (20 mg, 0.06 mmol) (Example 111 above) in a mixture of DMF/dioxane (2/7 mL respectively) was treated with aqueous HCl under vigorous stirring. (Z)-3-[(4-Acetyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-5-fluoro-4-[(2S,4R)-(4-hydroxy-pyrrolidin-2-yl)ethynyl]-2H-indol-2-one hydrochloride salt was obtained after lyophilization and treatment with THF and pentane. (Yield 20 mg, 91%).

Sources & evidence

ORD record
ord-f98a950026eb472ebd77abf3065e07e8
Source dataset
uspto-grants-2001_06
Patent number
US06252086B1

Reaction notes

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