Dimethylformamide → HCID 57449336, compound

HRID 1868022Notes

Reaction equation

HRID 1868022 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:17][CH:16]([CH3:18])[NH:15][CH2:14][CH:13]2[CH3:19])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl[C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][N:22]=1.C(N(C(C)C)CC)(C)C.CN(C=O)C>C(OCC)(=O)C>[Cl:27][C:26]1[C:21]([N:15]2[CH2:14][CH:13]([CH3:19])[N:12]([S:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)(=[O:11])=[O:10])[CH2:17][CH:16]2[CH3:18])=[N:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 169882,3-DichloropyridineHCID 81531DiisopropylethylamineHCID 64979891HCID 64979891, compound

Product 1

HCID 57449336HCID 57449336, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-(3,4-dichlorophenylsulfonyl)-2,5-dimethylpiperazine (1.04 g, 3.22 mmol), 2,3-dichloropyridine (476.5 mg. 3.22 mmol), diisopropylethylamine (1.4 mL, 8.05 mmol) and DMF (1.2 mL) were charged to a microwave vial and the mixture was irradiated at 200° C. for 1 hour. Reaction was complete as determined by TLC. The reaction mixture was diluted with ethyl acetate and washed with water. After solvent evaporation crude product was purified with flash column chromatography to yield 1-(3-chloropyridin-2-yl)-4-[(3,4-dichlorophenyl)sulfonyl]-2,5-dimethylpiperazine in 2% yield (27.1 mg) as yellow solid.

Workup

  1. customthe mixture was irradiated at 200° C. for 1 hour
  2. customReaction
  3. washwashed with water
  4. customAfter solvent evaporation crude product
  5. customwas purified with flash column chromatography

Sources & evidence

ORD record
ord-d172b090978b4058bd8c278f0fc1f327
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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