Dimethylamine, hydrochloride → HCID 10481025, compound

HRID 2300937Notes

Reaction equation

HRID 2300937 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:31])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[NH:17][C:18]([C:20]2[S:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[C:21]=2[CH2:29]Br)=[O:19])=[CH:4][CH:3]=1.Cl.[CH3:33][NH:34][CH3:35]>C(Cl)Cl.C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:31])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[NH:17][C:18]([C:20]2[S:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[C:21]=2[CH2:29][N:34]([CH3:35])[CH3:33])=[O:19])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 10473Dimethylamine, hydrochlorideHCID 18376709HCID 18376709, compound

Product 1

HCID 10481025HCID 10481025, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of N-(4-chlorophenyl)-2-[((3-(bromomethyl)benzo[b]thien-2-yl)carbonyl)amino]-5-chlorobenzamide (0.075 g, 0.14 mmol) in methylene chloride (1.5 mL) in a pressure vessel was added dimethylamine hydrochloride (0.035 g, 0.43 mmol), followed by Bio-Rad AG1-X8 anion exchange resin (0.55 g, 0.7 mmol equivalents, OH− form). The vessel was sealed and the mixture was stirred at ambient temperature for 3.5 hours. The vessel was opened and the reaction mixture diluted with methylene chloride (25 mL) and acetonitrile (25 mL), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel, followed by crystallization from acetonitrile afforded 0.030 g (43% yield) of N-(4-chlorophenyl)-2-[((3-(dimethylamino)methylbenzo[b]thien-2-yl)carbonyl)amino]-5-chlorobenzamide, as a crystalline solid; NMR (DMSO-d6/TFA) 13.2 (s, 1), 10.7 (s, 1), 7.3-8.1 (m, 11), 3.9 (s, 2), 2.1 (s, 6) ppm.

Workup

  1. customThe vessel was sealed
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography on silica gel
  5. customfollowed by crystallization from acetonitrile

Sources & evidence

ORD record
ord-0aa3508c9843447eb6eaf7aae800d38f
Source dataset
uspto-grants-2002_12
Patent number
US06498185B1

Reaction notes

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