Trimethylamine → HCID 53792392, compound

HRID 369407Notes

Reaction equation

HRID 369407 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH:25]=[CH2:26])(=[O:24])=[O:23])=[CH:17][CH:16]=3)=[CH:10][C:9]=2[CH3:27])=[O:7])=[CH:4][CH:3]=1.[CH2:30]([N:32](CC)[CH2:33]C)C.Cl.CNC.CN(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH2:25][CH2:26][N:32]([CH3:33])[CH3:30])(=[O:23])=[O:24])=[CH:17][CH:16]=3)=[CH:10][C:9]=2[CH3:27])=[O:7])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 1146TrimethylamineHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochloride2×HCID 54281356HCID 54281356, compound

Product 1

HCID 53792392HCID 53792392, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-{4-[5-(4-Chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]phenyl}-ethenesulfonamide (250 mg, 0.583 mmol) [prepared as in Example 19], was dissolved in DMF (1.1 ml). Triethylamine (0.11 ml, 0.8 mmol), followed by dimethylamine hydrochloride (36 mg, 0.69 mmol), was added and the reaction mixture was stirred for 1 h. A second batch of trimethylamine and dimethyamine hydrochloride was added and the stirring was continued overnight. The reaction mixture was partitioned between ethyl acetate and water, and the organic layer was separated and dried over sodium sulfate. The solvent was removed in vacuo and the crude product was then dissolved in ethyl acetate, after which ethanolic HCl was added to give N-{4-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]phenyl}-2-(dimethyl-amino)ethanesulfonamide (257 mg, 86%) as the hydrochloride salt.

Workup

  1. additionwas added
  2. waitthe stirring was continued overnight
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. customthe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed in vacuo
  7. dissolutionthe crude product was then dissolved in ethyl acetate
  8. additionafter which ethanolic HCl was added

Sources & evidence

ORD record
ord-840dbca4a5674f55b7c2b6299ae7d682
Source dataset
uspto-grants-2000_10
Patent number
US06136844

Reaction notes

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