proline dl-form → HCID 58392340, compound

HRID 561382Notes

Reaction equation

HRID 561382 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]1([CH3:20])[O:19][C:17](=[O:18])[CH2:16][C:14](=[O:15])[O:13]1.N1CCCC1C(O)=O.[F:29][C:30]1[CH:31]=[C:32]2[C:36](=[C:37]([CH2:39][S:40][CH3:41])[CH:38]=1)[NH:35][CH:34]=[CH:33]2>C(#N)C>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]([C:33]1[C:32]2[C:36](=[C:37]([CH2:39][S:40][CH3:41])[CH:38]=[C:30]([F:29])[CH:31]=2)[NH:35][CH:34]=1)[CH:16]1[C:17](=[O:18])[O:19][C:12]([CH3:20])([CH3:11])[O:13][C:14]1=[O:15]

Participants

6

Reactant 4

HCID 614proline dl-formHCID 134042,4-DichlorobenzaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 583922275-Fluoro-7-[(methylsulfanyl)methyl]-1H-indole

Product 1

HCID 58392340HCID 58392340, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.81 g (4.60 mmol) of 2,4-dichlorobenzaldehyde, 0.66 g (4.60 mmol) of Meldrum's acid and 25 mg (0.22 mmol) of D,L-proline were added to a solution of 0.95 g (4.38 mmol) of the compound from Example 11A in 36 ml of acetonitrile. The reaction mixture was stirred at RT overnight. It was concentrated to result in 3.10 g (97% of theory) of the title compound with a purity of 68% which were reacted without further purification.

Workup

  1. concentrationIt was concentrated

Sources & evidence

ORD record
ord-0062b61931c24b918ff9b8e86099ed4c
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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