2-Thiopheneacetyl chloride → HCID 10299477, compound

HRID 428708Notes

Reaction equation

HRID 428708 reaction equation
[NH2:1][C:2]1[C:3]([C:20]#[C:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=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].[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[CH2:33][C:34](Cl)=[O:35]>C1COCC1.C(=O)(O)[O-].[Na+]>[CH3:19][O:18][C:17]1[CH:16]=[CH:15][NH:14][C:13]=1/[CH:12]=[C:5]1\[C:6](=[O:11])[NH:7][C:8]2[C:4]\1=[C:3]([C:20]#[C:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[C:2]([NH:1][C:34](=[O:35])[CH2:33][C:29]1[S:28][CH:32]=[CH:31][CH:30]=1)=[CH:10][CH:9]=2

Participants

5

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 10108919HCID 10108919, compound

Product 1

HCID 10299477HCID 10299477, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Using Method M above, (Z)-5-amino-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-4-[(3-pyridinyl)ethynyl]-2H-indol-2-one (18 mg, 0.051 mmol) (from Example 69) was coupled with 2-thiopheneacetyl chloride (16.2 mg, 0.10 mmol) (Aldrich) in THF (2 mL) and saturated aqueous sodium bicarbonate (1 mL) at room temperature for 1 h, to yield (Z)-N-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-4-[(3-pyridinyl)ethynyl]-1H-indol-5-yl]-2-thiopheneacetamide. (Yield 7.7 mg, 32%).

Sources & evidence

ORD record
ord-a25a861f9691427486fd246680dc8bc6
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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