3-Methylbutanal → HCID 136374236, compound

HRID 601313Notes

Reaction equation

HRID 601313 reaction equation
[NH2:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:22][C:16]=3[S:15](=[O:32])(=[O:31])[N:14]=2)[C:3]1=[O:33].[CH:34](=O)[CH2:35][CH:36]([CH3:38])[CH3:37]>CN(C)C(=O)C>[CH2:24]([O:23][C:21]1[CH:20]=[CH:19][C:17]2[NH:18][C:13]([C:4]3[C:3](=[O:33])[N:2](/[N:1]=[CH:34]/[CH2:35][CH:36]([CH3:38])[CH3:37])[C:11]4[C:6]([C:5]=3[OH:12])=[CH:7][CH:8]=[CH:9][CH:10]=4)=[N:14][S:15](=[O:32])(=[O:31])[C:16]=2[CH:22]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 115523-MethylbutanalHCID 1363584841-amino-3-[7-(benzyloxy)-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl]-4-hydroxyquinolin-2(1H)-one

Product 1

HCID 136374236HCID 136374236, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
165 °C

Procedure

The product of Example 304F (0.220 g, 0.48 mmol) and isovaleraldehyde (0.77 mL, 7.18 mmol) in N,N-dimethylacetamide (1.5 mL) were reacted at 130° C. for 35 minutes in a microwave reactor in a sealed tube. The reaction was concentrated under a stream of nitrogen warmed through a manifold heated to 165° C. The resulting residue was triturated with diethyl ether and filtered to give the title compound (0.181 g, 72%).

Workup

  1. concentrationThe reaction was concentrated under a stream of nitrogen
  2. temperaturewarmed through a manifold
  3. customThe resulting residue was triturated with diethyl ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-3247c5e8d5f545a180ab601524cccaf1
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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