Pyridine → HCID 65480602, compound

HRID 1749352Notes

Reaction equation

HRID 1749352 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH2:13][C:14]1[C:15]([CH3:21])=[N:16][N:17]([CH3:20])[C:18]=1[CH3:19].N1C=CC=CC=1.CCOCC>C(Cl)Cl>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:13][C:14]2[C:15]([CH3:21])=[N:16][N:17]([CH3:20])[C:18]=2[CH3:19])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 1616031,3,5-trimethyl-1H-pyrazol-4-amineHCID 27344094-(Bromomethyl)benzenesulfonyl chloride

Product 1

HCID 65480602HCID 65480602, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromomethylbenzene sulfonyl chloride (3.72 g, 13.8 mmol) was added portionwise to a solution of 4-amino-1,3,5-trimethyl-1H-pyrazole (1.73 g, 13.8 mmol) and pyridine (1.5 ml) in DCM (100 ml) at rt. Concentration in vacuo gave a solid which was collected by vacuum filtration and washed with water (2×25 ml) then Et2O (100 ml) to give the title compound as a white solid (2.71 g, 7.59 mmol, 55%). δH (D-6 DMSO, 300K) 9.13 (1H, s), 7.64-7.55 (4H, m), 4.77 (2H, s), 3.55 (3H, s), 1.80 (3H, s), 1.54 (3H, s). m/z (ES+, 70V) 358.1 (MH+).

Workup

  1. concentrationConcentration in vacuo
  2. customgave a solid which
  3. filtrationwas collected by vacuum filtration
  4. washwashed with water (2×25 ml)

Sources & evidence

ORD record
ord-63bab0ac1fcb4344ab979884b9114610
Source dataset
uspto-grants-2015_10
Patent number
US09156811B2

Reaction notes

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