Butanal → HCID 136376453, compound

HRID 601222Notes

Reaction equation

HRID 601222 reaction equation
N[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)[CH2:26][CH2:27][CH3:28].C[N:31](C)C(=O)C>>[CH:25](=[N:31][C:23]1[S:22][C:4]2[C:5]([OH:21])=[C:6]([C:9]3[NH:14][C:13]4[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=4[S:11](=[O:20])(=[O:19])[N:10]=3)[C:7](=[O:8])[NH:2][C:3]=2[CH:24]=1)[CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 3

HCID 261ButanalHCID 31374DimethylacetamideHCID 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 136376453HCID 136376453, compoundYield 65%

Conditions

Temperature
25 °C

Procedure

The product of Example 268D (0.10 g, 0.27 mmol) was reacted with butyraldehyde (0.5 g, 6.9 mmol) in N,N-dimethylacetamide (3 mL) in a sealed tube at 130° C. for 40 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 (0.075 g, 65%).

Workup

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

Sources & evidence

ORD record
ord-9fe2a72f9f1c4dcda89964d8bdda698b
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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