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

HRID 1069753Notes

Reaction equation

HRID 1069753 reaction equation
[F:1][C:2]1[C:3]([C:20]#[C:21][C@@H:22]2[CH2:26][C@@H:25]([OH:27])[CH2:24][NH:23]2)=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]\[C:13]1[NH:14][CH:15]=[CH:16][C:17]=1[O:18][CH3:19].Cl.C(Cl)[Cl:30].CO>CN(C=O)C>[ClH:30].[F:1][C:2]1[C:3]([C:20]#[C:21][C@@H:22]2[CH2:26][C@@H:25]([OH:27])[CH2:24][NH:23]2)=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:12]\[C:13]1[NH:14][CH:15]=[CH:16][C:17]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226129Dichloromethane methanolHCID 23645083(3Z)-5-fluoro-4-{2-[(2S,4R)-4-hydroxypyrrolidin-2-yl]ethynyl}-3-[(3-methoxy-1H-pyrrol-2-yl)methylidene]-2,3-dihydro-1H-indol-2-one

Product 1

HCID 69949280(z)-1,3-Dihydro-5-fluoro-4-[(2s,4r)-(4-hydroxy-pyrrolidin-2-yl)-ethynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylene]-2h-indol-2-one hydrochloride salt

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (Z)-1,3-dihydro-5-fluoro-4-[(2S,4R)-(4-hydroxy-pyrrolidin-2-yl)-ethynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (30 mg, 0.06 mmol) (Example 99D above) in DMF (3 mL) was treated with aqueous HCl under vigorous stirring. The solution was lyophilized and the residue was perceipitated from a mixture of CH2Cl2/MeOH (3:1) with excess of pentanes. (Yield 30 mg, 91%).

Sources & evidence

ORD record
ord-882d5295c5ff4489ba047a076438aac2
Source dataset
uspto-grants-2001_06
Patent number
US06252086B1

Reaction notes

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