2-Amino-thiazole-5-carboxylic acid ethyl ester → HCID 21111660, compound

HRID 1766602Notes

Reaction equation

HRID 1766602 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][O:5][C:6]1[CH:15]=[C:14]([C:16]([OH:18])=O)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:19])[CH:12]=2)[N:7]=1.[NH2:24][C:25]1[S:26][C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][N:29]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][O:5][C:6]1[CH:15]=[C:14]([C:16](=[O:18])[NH:24][C:25]2[S:26][C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][N:29]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:19])[CH:12]=2)[N:7]=1

Participants

7

Reactant 3

HCID 3146282-Amino-thiazole-5-carboxylic acid ethyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21111658HCID 21111658, compound

Product 1

HCID 21111660HCID 21111660, compoundYield 19.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(2-chlorobenzyloxy)-4-carboxy-6-methylquinoline (Method 7; 0.350 g, 1.067 mmol) and ethyl 2-aminothiazole-5-carboxylate (0.184 g, 1.067 mmol) in dimethyl formamide (DMF, 6 ml) was added 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (0.307 g, 1.601 mmol) and 4-dimethylaminopyridine (0.391 g, 3.202 mmol). The reaction mixture was stirred overnight at room temperature, and then diluted with ethyl acetate (20 ml). The mixture was washed with water (20 ml), and the aqueous washings extracted with ethyl acetate (3×15 ml); the organic phases were combined and concentrated in vacuo. Flash chromatography on silica gel, eluting with a gradient of 2–20% ethyl acetate in iso-hexane, gave the title compound as a colourless solid (0.100 g, 19%). NMR: 1.30 (3H, t), 2.40 (3H, s), 4.30 (2H, q), 6.65 (2H, d), 7.20 (2H, m), 7.55 (2H, m), 7.65 (1H, m), 7.75 (1H, d), 7.95 (1H, s), 8.10 (2H, m), 8.15 (1H, s); m/z 482 (M+H)+, 480 (M−H)+,

Workup

  1. washThe mixture was washed with water (20 ml)
  2. extractionthe aqueous washings extracted with ethyl acetate (3×15 ml)
  3. concentrationconcentrated in vacuo
  4. washFlash chromatography on silica gel, eluting with a gradient of 2–20% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-7cc2aab68d5d4e7487b166a488fdba1f
Source dataset
uspto-grants-2007_06
Patent number
US07230108B2

Reaction notes

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