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

HRID 561430Notes

Reaction equation

HRID 561430 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:14][C:15]1([CH3:23])[O:22][C:20](=[O:21])[CH2:19][C:17](=[O:18])[O:16]1.N1CCCC1C(O)=O.[CH3:32][S:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[C:39]2[C:43]=1[NH:42][CH:41]=[CH:40]2>C(#N)C>[Cl:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]([C:40]1[C:39]2[C:43](=[C:35]([CH2:34][S:33][CH3:32])[CH:36]=[CH:37][CH:38]=2)[NH:42][CH:41]=1)[CH:19]1[C:20](=[O:21])[O:22][C:15]([CH3:23])([CH3:14])[O:16][C:17]1=[O:18]

Participants

6

Reactant 4

HCID 614proline dl-formHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 130761442-Chloro-4-(trifluoromethyl)benzaldehydeHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583922325-([2-Chloro-4-(trifluoromethyl)phenyl]{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.50 g (7.19 mmol) of 2-chloro-4-(trifluoromethyl)benzaldehyde, 1.04 g (7.19 mmol) of Meldrum's acid and 39.4 mg (0.34 mmol) of D,L-proline were added to a solution of 1.21 g (6.85 mmol) of the compound from Example 8A in 57 ml of acetonitrile. The reaction mixture was stirred at RT overnight. It was concentrated, and the residue was taken up in diethyl ether and again concentrated. 3.64 g (75% of theory, 72% purity) of the title compound were obtained and were reacted without further purification.

Workup

  1. concentrationIt was concentrated
  2. concentrationagain concentrated

Sources & evidence

ORD record
ord-6d67790b25ed4da09e1e991448c54c6b
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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