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

HRID 601266Notes

Reaction equation

HRID 601266 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.[CH3:25][C@@H:26]1[CH2:31][CH2:30][CH2:29][C:28](=O)[CH2:27]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]=[C:28]3[CH2:29][CH2:30][CH2:31][C@@H:26]([CH3:25])[CH2:27]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 83384(+)-3-MethylcyclohexanoneHCID 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 1363741076-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-7-hydroxy-4-{[(3R)-3-methylcyclohexylidene]amino}thieno[3,2-b]pyridin-5(4H)-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
25 °C

Procedure

The product of Example 268D (0.073 g, 0.2 mmol) was reacted with (3R)-3-methylcyclohexanone (1.12 g, 10.0 mmol) in N,N-dimethylacetamide (2 mL) in a sealed tube at 135° C. for 45 minutes in a microwave reactor. The reaction was cooled to 25° C. and concentrated under vacuum. The resulting residue was triturated with diethyl ether (3 mL) and filtered to give the title compound.

Workup

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

Sources & evidence

ORD record
ord-7a88e82323f34c8e9c1de30b437644f2
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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