Methanesulfonamide → HCID 57799247, compound

HRID 1516298Notes

Reaction equation

HRID 1516298 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:19][C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][N:21]=2)[C:5]2[N:10]([CH2:11][CH2:12][O:13][CH2:14][CH3:15])[N:9]=[C:8]([C:16](O)=[O:17])[C:6]=2[N:7]=1.[CH3:27][S:28]([NH2:31])(=[O:30])=[O:29].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.CN(C)C=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:19][C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][N:21]=2)[C:5]2[N:10]([CH2:11][CH2:12][O:13][CH2:14][CH3:15])[N:9]=[C:8]([C:16]([NH:31][S:28]([CH3:27])(=[O:30])=[O:29])=[O:17])[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 72879Methanesulfonamide3×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride3×HCID 59777540HCID 59777540, compound

Product 1

HCID 57799247HCID 57799247, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst3×HCID 6228DimethylformamideSolvent

Procedure

The carboxylic acid of Step 8 (1.0 g, 2.70 mmol), methanesulphonamide (330 mg, 3.5 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (660 mg, 3.5 mmol) and 4-dimethylaminopyridine (390 mg, 3.5 mmol) were dissolved in N,N-dimethylformamide (10 mL) and the reaction mixture stirred at room temperature for 60 hours. Additional methanesulphonamide (165 mg, 1.7 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (330 mg, 1.7 mmol) and 4-dimethylaminopyridine (195 mg, 1.7 mmol) were added and the reaction mixture stirred for a further 20 hours. Further methanesulphonamide (165 1.7 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (330 mg, 1.7 mmol) and 4-dimethylaminopyridine (195 mg 1.7 mmol) were added and the reaction mixture stirred for a final 18 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between dichloromethane (25 mL) and water (25 mL). The organic phase was separated, washed with water (2×25 mL), dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:acetic acid 100:0:0 to 96:3.5:0.5. The crude product was triturated in warm ethyl acetate (10 mL) to yield the title product, 290 mg.

Workup

  1. stirringthe reaction mixture stirred for a further 20 hours
  2. stirringthe reaction mixture stirred for a final 18 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue partitioned between dichloromethane (25 mL) and water (25 mL)
  5. customThe organic phase was separated
  6. washwashed with water (2×25 mL)
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:acetic acid 100:0:0 to 96:3.5:0.5
  10. customThe crude product was triturated in warm ethyl acetate (10 mL)

Sources & evidence

ORD record
ord-c942de9e20c7411a82e56d98f8970b6f
Source dataset
uspto-grants-2012_07
Patent number
US08227475B2

Reaction notes

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