4-Pyridinecarboxaldehyde → 6-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-7-hydroxy-4-{[pyridin-4-ylmethylene]amino}thieno[3,2-b]pyridin-5(4H)-one

HRID 601240Notes

Reaction equation

HRID 601240 reaction equation
[NH2:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[S:11](=[O:20])(=[O:19])[N:10]=2)=[C:5]([OH:21])[C:4]2[S:22][CH:23]=[CH:24][C:3]1=2.[CH:25](=O)[C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1>CN(C)C(=O)C>[O:19]=[S:11]1(=[O:20])[C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[NH:14][C:9]([C:6]2[C:7](=[O:8])[N:2]([N:1]=[CH:25][C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)[C:3]3[CH:24]=[CH:23][S:22][C:4]=3[C:5]=2[OH:21])=[N:10]1

Participants

4

Reactant 2

HCID 133894-PyridinecarboxaldehydeHCID 1363736274-amino-6-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-7-hydroxythieno[3,2-b]pyridin-5(4H)-one

Product 1

HCID 1363742276-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-7-hydroxy-4-{[pyridin-4-ylmethylene]amino}thieno[3,2-b]pyridin-5(4H)-oneYield 76.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
25 °C

Procedure

The product of Example 268D (0.10 g, 0.27 mmol) was reacted with isonicotinaldehyde (0.5 g, 4.7 mmol) in N,N-dimethylacetamide (3 mL) in a sealed tube at 135° C. for 60 minutes in a microwave reactor. The reaction was cooled to 25° C. and concentrated under vacuum. The resulting residue was triturated with diethyl ether and filtered to give the title compound (0.093 g, 76%).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe resulting residue was triturated with diethyl ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-068714f826db4cb6b3c228fc0fbc1f49
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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