Potassium Carbonate → 1-[2-Oxo-2-(3-oxo-3,4dihydro-2H-benzo[1,4]thiazin-6yl)-ethyl]-piperidine-4-carboxylic acid (6-methoxy-[1,5]naphthyridin 4yl)-amide oxalate

HRID 456602Notes

Reaction equation

HRID 456602 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[NH:13][C:14]([CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:15].[C:22](=[O:25])([O-:24])[O-].[K+].[K+].Cl[CH2:29][C:30]([C:32]1[CH:33]=[CH:34][C:35]2[S:40][CH2:39][C:38](=[O:41])[NH:37][C:36]=2[CH:42]=1)=[O:31].CO.[C:45]([O:48]CC)(=[O:47])C>CN(C)C=O>[C:45]([OH:48])(=[O:47])[C:22]([OH:24])=[O:25].[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[NH:13][C:14]([CH:16]1[CH2:21][CH2:20][N:19]([CH2:29][C:30](=[O:31])[C:32]2[CH:33]=[CH:34][C:35]3[S:40][CH2:39][C:38](=[O:41])[NH:37][C:36]=3[CH:42]=2)[CH2:18][CH2:17]1)=[O:15]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 11231497Piperidine-4-carboxylic acid (6-methoxy-[1,5]naphthyridin-4-yl)-amideHCID 162180756-(Chloroacetyl)-2H-1,4-benzothiazin-3(4H)-oneHCID 21584119Ethylacetate methanol

Product 1

HCID 1317262831-[2-Oxo-2-(3-oxo-3,4dihydro-2H-benzo[1,4]thiazin-6yl)-ethyl]-piperidine-4-carboxylic acid (6-methoxy-[1,5]naphthyridin 4yl)-amide oxalate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of piperidine (1f) (0.39 g) and potassium carbonate (0.2 g) in N,N-dimethylformamide (13 ml) was treated with (a) (0.33 g). After 7 hours the mixture was evaporated and the residue partitoned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic extract was dried and evaporated to give a brown oil. Chromatography on silica eluting with a methanol/ethyl acetate gradient afforded the free base of the title compound as an oil (0.19 g).

Workup

  1. customAfter 7 hours the mixture was evaporated
  2. extractionThe organic extract
  3. customwas dried
  4. customevaporated
  5. customto give a brown oil

Sources & evidence

ORD record
ord-706ffe303b33424490fe5d355eb141af
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

Loading…