Tetrahydrofuran → (Z)-N-[2,3-dihydro-4-(3-hydroxy-1-propynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-5-yl]-4-pyridinecarboxamide

HRID 366669Notes

Reaction equation

HRID 366669 reaction equation
[NH2:1][C:2]1[C:3]([C:20]#[C:21][CH2:22][OH:23])=[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].[CH2:24](Cl)[C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1.C1C[O:35]CC1>>[OH:23][CH2:22][C:21]#[C:20][C:3]1[C:2]([NH:1][C:24]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[O:35])=[CH:10][CH:9]=[C:8]2[C:4]=1/[C:5](=[CH:12]/[C:13]1[NH:14][CH:15]=[CH:16][C:17]=1[O:18][CH3:19])/[C:6](=[O:11])[NH:7]2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 745714-(Chloromethyl)pyridineHCID 9883118(Z)-5-amino-1,3-dihydro-4-(3-hydroxy-1-propynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Product 1

HCID 18366050(Z)-N-[2,3-dihydro-4-(3-hydroxy-1-propynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-5-yl]-4-pyridinecarboxamide

Procedure

Using Method M above, (Z)-5-amino-1,3-dihydro-4-(3-hydroxy-1-propynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (20 mg, 0.065 mmol) (from Example 32 above) was acylated with isonicotinyl chloride (23 mg, 0.13 mmol) (Aldrich) in THF (2 mL) at room temperature for 10 days to give (Z)-N-[2,3-dihydro-4-(3-hydroxy-1-propynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-5-yl]-4-pyridinecarboxamide. (Yield 10 mg, 37%).

Sources & evidence

ORD record
ord-9c42f0c650f7493f9953d54f472adcd4
Source dataset
uspto-grants-2000_10
Patent number
US06130239

Reaction notes

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