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

HRID 366746Notes

Reaction equation

HRID 366746 reaction equation
[C:1]([C:4]1[CH:5]=[C:6](/[CH:9]=[C:10]2\[C:11](=[O:27])[NH:12][C:13]3[C:18]\2=[C:17]([C:19]#[C:20][C@@H:21]2[CH2:25][CH2:24][CH2:23][NH:22]2)[C:16]([F:26])=[CH:15][CH:14]=3)[NH:7][CH:8]=1)(=[O:3])[CH3:2].[ClH:28]>O1CCOCC1>[ClH:28].[C:1]([C:4]1[CH:5]=[C:6](/[CH:9]=[C:10]2\[C:11](=[O:27])[NH:12][C:13]3[C:18]\2=[C:17]([C:19]#[C:20][C@@H:21]2[CH2:25][CH2:24][CH2:23][NH:22]2)[C:16]([F:26])=[CH:15][CH:14]=3)[NH:7][CH:8]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59959920(S)-(Z)-3-[(4-Acetyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-5-fluoro-4-[(pyrrolidin-2-yl)ethynyl]-2H-indol-2-one

Product 1

HCID 69951147(s)-(z)-3-[(4-Acetyl-1h-pyrrol-2-yl)methylene]-1,3-dihydro-5-fluoro-4-[(pyrrolidin-2-yl)ethynyl]-2h-indol-2-one hydrochloride salt

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (S)-(Z)-3-[(4-acetyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-5-fluoro-4-[(pyrrolidin-2-yl)ethynyl]-2H-indol-2-one (25 mg, 0.07 mmol) (Example 109 above) in dioxane (3 mL) was treated with aqueous HCl under vigorous stirring. (S)-(Z)-3-[(4-Acetyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-5-fluoro-4-[(pyrrolidin-2-yl)ethynyl]-2H-indol-2-one hydrochloride salt was obtained upon lyophilization of this solution. (Yield 24 mg, 76%).

Sources & evidence

ORD record
ord-98710a21ace34f368eff4cc92a6e1c56
Source dataset
uspto-grants-2000_10
Patent number
US06130239

Reaction notes

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