Dimethylamine → HCID 18376983, compound

HRID 370119Notes

Reaction equation

HRID 370119 reaction equation
[CH3:1][NH:2][CH3:3].[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:41])[C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([O:20][CH3:21])[C:14]=2[NH:22][C:23]([C:25]2[S:26][CH:27]=[C:28]([CH2:31][C:32]3[N:36]=[C:35](C(Cl)(Cl)Cl)[O:34][N:33]=3)[C:29]=2[Cl:30])=[O:24])=[N:9][CH:10]=1.O>CN(C=O)C>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:41])[C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([O:20][CH3:21])[C:14]=2[NH:22][C:23]([C:25]2[S:26][CH:27]=[C:28]([CH2:31][C:32]3[N:36]=[C:35]([N:2]([CH3:3])[CH3:1])[O:34][N:33]=3)[C:29]=2[Cl:30])=[O:24])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 18376776HCID 18376776, compound

Product 1

HCID 18376983HCID 18376983, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethylamine (40% aqueous, 0.51 mL, 4.1 mmol) was dissolved in DMF (2 mL) under nitrogen, and N-(5-chloropyridin-2-yl)-2-[((4-((5-trichloromethyl-1,2,4-oxadiazol-3-yl)methyl)-3-chlorothiophen-2-yl)carbonyl)amino]-3-methoxy-5-chlorobenzamide (0.151 g, 0.23 mmol) was added. The reaction mixture was stirred for 40 minutes at ambient temperature, then poured into water (40 mL). The aqueous layer was extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with water (3×25 mL), brine (25 mL), dried over magnesium sulfate, concentrated in vacuo, and dried under vacuum. The crude product was purified by flash chromatography on silica gel, eluting with 75% ethyl acetate/hexanes to afford N-(5-chloropyridin-2-yl)-2-[((4-((5-(dimethylamino)-1,2,4-oxadiazol-3-yl)methyl)-3-chlorothiophen-2-yl)carbonyl)amino]-3-methoxy-5-chlorobenzamide; NMR (DMSO-d6) 10.9 (br, 1), 9.4 (br, 1), 8.4 (d, 1), 8.1 (d, 1), 7.9 (dd, 1), 7.8 (s, 1), 7.4 (d, 1), 7.2 (d, 1), 3.9 (s, 3), 3.8 (s, 2), 3.0 (s, 6) ppm.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (3×25 mL)
  2. washThe combined organic layers were washed with water (3×25 mL), brine (25 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customdried under vacuum
  6. customThe crude product was purified by flash chromatography on silica gel
  7. washeluting with 75% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-815b7ee3bd08470780ca55008a75ff32
Source dataset
uspto-grants-2000_10
Patent number
US06140351

Reaction notes

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