Ethanol → HCID 86606577, compound

HRID 2244457Notes

Reaction equation

HRID 2244457 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[N:12]=[C:13]([CH3:17])[S:14][C:15]=2[NH2:16])=[O:10])[CH:5]=[CH:4][N:3]=1.[CH:18]1([CH:21]=O)[CH2:20][CH2:19]1.C(O)C.C([BH3-])#N.[Na+]>O>[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[N:12]=[C:13]([CH3:17])[S:14][C:15]=2[NH:16][CH2:21][CH:18]2[CH2:20][CH2:19]2)=[O:10])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 123114CyclopropanecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 866065745-Amino-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide

Product 1

HCID 86606577HCID 86606577, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Amino-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide (0.200 g, 0.806 mmol) was treated with cyclopropanecarboxaldehyde (0.230 g, 3.22 mmol) and tetraisopropyl-orthotitanate (0.916 g, 3.22 mmol) and stirred at room temperature overnight. Ethanol (5 mL) and sodium cyanoborohydride (0.213 g, 3.22 mmol) were added and the reaction mixture was stirred for 5 h. Water (0.5 mL) was added to the reaction mixture and the solvent was evaporated. The residue was purified by flash chromatography on silica gel with ethyl acetate/methanol 100:0→90:10 gradient to yield the title compound (0.110 g, 45%) as a light yellow solid, MS (ISP): m/e=303.1 (M+H+).

Workup

  1. stirringthe reaction mixture was stirred for 5 h
  2. customthe solvent was evaporated
  3. customThe residue was purified by flash chromatography on silica gel with ethyl acetate/methanol 100:0→90:10 gradient

Sources & evidence

ORD record
ord-725797ff424a4ddabea9797abae96dc2
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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