Potassium Carbonate → [(3-{1-[(cyclopropylmethyl)amino]-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl}-8-nitro-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl)oxy]acetonitrile

HRID 601365Notes

Reaction equation

HRID 601365 reaction equation
[CH:1]1([CH2:4][NH:5][N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([OH:16])=[C:8]([C:17]3[NH:22][C:21]4[CH:23]=[CH:24][C:25]([OH:30])=[C:26]([N+:27]([O-:29])=[O:28])[C:20]=4[S:19](=[O:32])(=[O:31])[N:18]=3)[C:7]2=[O:33])[CH2:3][CH2:2]1.Br[CH2:35][C:36]#[N:37].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]1([CH2:4][NH:5][N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([OH:16])=[C:8]([C:17]3[NH:22][C:21]4[CH:23]=[CH:24][C:25]([O:30][CH2:35][C:36]#[N:37])=[C:26]([N+:27]([O-:29])=[O:28])[C:20]=4[S:19](=[O:32])(=[O:31])[N:18]=3)[C:7]2=[O:33])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 1363584201-[(cyclopropylmethyl)amino]-4-hydroxy-3-(7-hydroxy-8-nitro-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)quinolin-2(1H)-one

Product 1

HCID 136358422[(3-{1-[(cyclopropylmethyl)amino]-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl}-8-nitro-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl)oxy]acetonitrileYield 60.6%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

The product of Example 381 (20 mg, 0.042 mmol) in N,N-dimethylformamide (2 mL) was reacted with 2-bromoacetonitrile (6 μl, 0.086 mmol), potassium carbonate (54.7 mg, 0.168 mmol) and tetrabutylammonium iodide (catalytic) at 25° C. for 18 hours. The solution was evaporated under reduced pressure and the residue was triturated with ethyl acetate, filtered and washed with water to give the title compound (13 mg, 60%).

Workup

  1. customThe solution was evaporated under reduced pressure
  2. customthe residue was triturated with ethyl acetate
  3. filtrationfiltered
  4. washwashed with water

Sources & evidence

ORD record
ord-9fc871ee4cb248d79d57b4cda56e37bd
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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