Cyclopropanecarboxaldehyde → HCID 136358483, compound

HRID 601274Notes

Reaction equation

HRID 601274 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]1([CH:28]=O)[CH2:27][CH2:26]1>CN(C)C(=O)C>[CH:25]1([CH:28]=[N:1][N:2]2[C:7](=[O:8])[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:5]([OH:21])[C:4]3[S:22][CH:23]=[CH:24][C:3]2=3)[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 123114CyclopropanecarboxaldehydeHCID 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 136358483HCID 136358483, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
25 °C

Procedure

The product of Example 268D (0.15 g, 0.41 mmol) was reacted with cyclopropanecarbaldehyde (1.0 g, 14 mmol) in N,N-dimethylacetamide (3 mL) in a sealed tube at 120° C. for 90 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 (0.104 g, 60%).

Workup

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

Sources & evidence

ORD record
ord-893dfe9547f24fe788c4a3e39dd53ee5
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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