2,4-Dimethyl-1,3-thiazole-5-carbaldehyde → Methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(2,4-dimethyl-1,3-thiazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate

HRID 587068Notes

Reaction equation

HRID 587068 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[CH2:20][C:19]=3[CH:29]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[CH3:30][C:31]1[S:32][C:33]([CH:37]=O)=[C:34]([CH3:36])[N:35]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:37][C:33]4[S:32][C:31]([CH3:30])=[N:35][C:34]=4[CH3:36])[CH2:23][CH2:22][C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:20][C:19]=3[CH:29]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 27762492,4-Dimethyl-1,3-thiazole-5-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69749802Methyl 7-[4-(2-butoxyethoxy)phenyl]-1-benzazepine-4-carboxylate

Product 1

HCID 22329187Methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(2,4-dimethyl-1,3-thiazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylateYield 28.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In 1,2-dichloroethane (21 ml) was dissolved methyl 7-[4-(2-butoxyethoxy)phenyl]-1-benzazepine-4-carboxylate (0.70 g). To the solution were added 2,4-dimethyl-1,3-thiazole-5-carbaldehyde (0.62 g) and sodium triacetoxyborohydride (1.5 g), and the mixture was stirred at room temperature for 36 hours. After stirred at 60° C. for 12 hours, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=1/1) to give methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(2,4-dimethyl-1,3-thiazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate (0.26 g).

Workup

  1. stirringAfter stirred at 60° C. for 12 hours
  2. temperaturethe mixture was cooled to room temperature
  3. customthe solvent was removed under reduced pressure
  4. additionThe residue was added to water
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried with magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-de3b43309eb94767a19e06c10f7c40cf
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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