Dimethylamine, hydrochloride → HCID 10481025, compound

HRID 370108Notes

Reaction equation

HRID 370108 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 AGI-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-9d2f751fe16b42c496fa09bc08fb636e
Source dataset
uspto-grants-2000_10
Patent number
US06140351

Reaction notes

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