Propane, 1,1-diethoxy- → 3-[7-(benzyloxy)-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl]-4-hydroxy-1-[propylideneamino]quinolin-2(1H)-one

HRID 601348

Reaction equation

HRID 601348 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].C(O[CH:37](OCC)[CH2:38][CH3:39])C>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:37][CH2:38][CH3:39])[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 20858Propane, 1,1-diethoxy-HCID 1363584841-amino-3-[7-(benzyloxy)-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl]-4-hydroxyquinolin-2(1H)-one

Product 1

HCID 1363584163-[7-(benzyloxy)-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl]-4-hydroxy-1-[propylideneamino]quinolin-2(1H)-oneYield 42%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
25 °C

Procedure

The product of Example 304F (0.1 g, 0.22 mmol) in N,N-dimethylacetamide (1 mL) was reacted with propionaldehyde diethylacetal (0.34 mL, 2.2 mmol) in a sealed tube in a microwave reactor at 100° C. for 60 minutes. The reaction was cooled to 25° C., concentrated under a stream of nitrogen warmed through a manifold heated to 165° C. and the resulting residue was triturated with diethyl ether to give the title compound (0.045 g, 42%).

Workup

  1. concentrationconcentrated under a stream of nitrogen
  2. temperaturewarmed through a manifold
  3. temperatureheated to 165° C.
  4. customthe resulting residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-24cb7fa830164d88983a2d929e9f0d37
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Linked notes

Loading…