Cyclopropanecarboxaldehyde → 1-{[cyclopropylmethylene]amino}-4-hydroxy-3-{7-[(methoxymethoxy)methyl]-1,1-dioxido-4H-thieno[2,3-e][1,2,4]thiadiazin-3-yl}quinolin-2(1H)-one

HRID 601332Notes

Reaction equation

HRID 601332 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([N:12]2C(=O)[C:19]3[C:14](=[CH:15]C=CC=3)[C:13]2=O)[C:4](=[O:23])[C:3]=1[C:24]1[NH:29][C:28]2[S:30][CH:31]=[C:32]([CH2:33][O:34][CH2:35][O:36][CH3:37])[C:27]=2[S:26](=[O:39])(=[O:38])[N:25]=1.C1(C=O)CC1>CN(C)C(=O)C>[CH:14]1([CH:13]=[N:12][N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([OH:1])=[C:3]([C:24]3[NH:29][C:28]4[S:30][CH:31]=[C:32]([CH2:33][O:34][CH2:35][O:36][CH3:37])[C:27]=4[S:26](=[O:38])(=[O:39])[N:25]=3)[C:4]2=[O:23])[CH2:15][CH2:19]1

Participants

4

Reactant 2

HCID 123114CyclopropanecarboxaldehydeHCID 1363584122-[4-hydroxy-3-{7-[(methoxymethoxy)methyl]-1,1-dioxido-4H-thieno[2,3-e][1,2,4]thiadiazin-3-yl}-2-oxoquinolin-1(2H)-yl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 1363584131-{[cyclopropylmethylene]amino}-4-hydroxy-3-{7-[(methoxymethoxy)methyl]-1,1-dioxido-4H-thieno[2,3-e][1,2,4]thiadiazin-3-yl}quinolin-2(1H)-oneYield 75%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
25 °C

Procedure

The product of Example 350D (94 mg, 0.22 mmol) was reacted with cyclopropanecarbaldehyde (0.162 mL, 2.2 mmol) in N,N-dimethylacetamide (1 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 reduced pressure. The resulting residue was triturated with diethyl ether and filtered to give the title compound (78.9 mg, 75%).

Workup

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

Sources & evidence

ORD record
ord-b4435d0108a54fd78f2145f10d7a4fed
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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