Ethanol → HCID 86671252, compound

HRID 1952553Notes

Reaction equation

HRID 1952553 reaction equation
Cl[C:2]1[S:3][C:4]([C:8]([O:10][CH2:11]C)=[O:9])=[C:5]([CH3:7])[N:6]=1.[NH:13]1[C:21]2[C:16](=[C:17]([CH2:22][CH2:23][CH2:24][NH2:25])[CH:18]=[CH:19][CH:20]=2)[CH:15]=[N:14]1.C([O-])(=O)C.[K+].C(O)C>C(OCC)(=O)C.O>[CH3:11][O:10][C:8]([C:4]1[S:3][C:2]([NH:25][CH2:24][CH2:23][CH2:22][C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:16]=2[CH:15]=[N:14][NH:13]3)=[N:6][C:5]=1[CH3:7])=[O:9]

Participants

7

Reactant 4

HCID 702EthanolHCID 517044Potassium AcetateHCID 594903Ethyl 2-chloro-4-methyl-1,3-thiazole-5-carboxylateHCID 68226750HCID 68226750, compound

Product 1

HCID 86671252HCID 86671252, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 2-chloro-4-methyl-1,3-thiazole-5-carboxylate (0.28 g, 1.361 mmol), 3-(1H-Indazol-4-yl)-propylamine (300 mg, 1.712 mmol), potassium acetate (180 mg, 1.834 mmol) and ethanol (3 mL) was microwaved for 90 min. at 160° C. The reaction is diluted with ethyl acetate (150 mL) and water (30 mL). and washed with brine (2×30 mL), dried over anhydrous magnesium sulfate, filtered, concentrated to give 2-[3-(1H-Indazol-4-yl)-propylamino]-4-methyl-thiazole-5-carboxylic acid methyl ester (0.230 g, 49%)) as a yellow solid. MS m/e 331.4 (M+H+).

Workup

  1. customwas microwaved for 90 min. at 160° C
  2. washand washed with brine (2×30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-460405a536b147aa8a91921591bbe010
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

Loading…