2-Dimethylaminopyridine → HCID 73986452, compound

HRID 841899Notes

Reaction equation

HRID 841899 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH:18]=[C:19]1[S:23][C:22](=[O:24])[NH:21][C:20]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1[Cl:36])[C:30](Cl)=[O:31].CN(C1C=CC=CN=1)C>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:30](=[O:31])[C:29]1[CH:33]=[CH:34][C:35]([Cl:36])=[C:27]([Cl:26])[CH:28]=1)[CH:13]=[C:12]2[CH:18]=[C:19]1[S:23][C:22](=[O:24])[NH:21][C:20]1=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 178518467HCID 178518467, compound

Product 1

HCID 73986452HCID 73986452, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Benzyloxy-3-(2,4-dioxo-thiazolidin-5-ylidene-methyl)-indole (Example 1, Step A; 10 mg) was dissolved in pyridine (1.5 mL) and 3,4-dichlorobenzoyl chloride (35 mg) and a trace of dimethylaminopyridine were added. The mixture was stirred at 50-60° for 18 hrs until the reaction was determined to be complete by TLC. Volatiles were removed under reduced pressure and the residue was washed with water and ether; 10 mg; consistent nmr and ms (m\e 525 (M+1); greater than 95% by HPLC.

Workup

  1. customVolatiles were removed under reduced pressure
  2. washthe residue was washed with water and ether

Sources & evidence

ORD record
ord-8d1075146c6f4a31ba637698e284936e
Source dataset
uspto-grants-2002_04
Patent number
US06372742B1

Reaction notes

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