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 1069691Notes

Reaction equation

HRID 1069691 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-bac50eb320864afd8967bdc85d2d3333
Source dataset
uspto-grants-2001_06
Patent number
US06252086B1

Reaction notes

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