proline dl-form → 5-[(2-Bromo-1,3-thiazol-5-yl){7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 561388

Reaction equation

HRID 561388 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.N1CCCC1C(O)=O.[Br:19][C:20]1[S:21][C:22]([CH:25]=O)=[CH:23][N:24]=1.[CH3:27][S:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]2[C:38]=1[NH:37][CH:36]=[CH:35]2>C(#N)C>[Br:19][C:20]1[S:21][C:22]([CH:25]([C:35]2[C:34]3[C:38](=[C:30]([CH2:29][S:28][CH3:27])[CH:31]=[CH:32][CH:33]=3)[NH:37][CH:36]=2)[CH:6]2[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]2=[O:5])=[CH:23][N:24]=1

Participants

6

Reactant 4

HCID 614proline dl-formHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 27732592-Bromo-1,3-thiazole-5-carbaldehydeHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583922715-[(2-Bromo-1,3-thiazol-5-yl){7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.02 g (7.08 mmol) of Meldrum's acid, 0.04 g (0.34 mmol) of D,L-proline and 1.36 g (7.08 mmol) of 2-bromo-5-formylthiazole were successively added to a solution of 1.30 g (6.75 mmol) of the compound from Example 8A in 50 ml of acetonitrile. The reaction mixture was stirred at RT overnight and then the solvent was removed in vacuo. Purification of the residue by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 95/5) resulted in 3.58 g (81% purity, 87% of theory) of the title compound.

Workup

  1. customthe solvent was removed in vacuo
  2. customPurification of the residue by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 95/5)

Sources & evidence

ORD record
ord-f7633072c4254390973e72a6a89551ba
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Linked notes

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