Boron tribromide → HCID 178464669, compound

HRID 2273963Notes

Reaction equation

HRID 2273963 reaction equation
[CH2:1]([NH:3][C:4]([N:17]1[CH2:21][CH:20]([CH2:22][CH3:23])[CH:19]=[N:18]1)=[N:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([NH:3][C:4]([N:17]1[CH2:21][CH:20]([CH2:22][CH3:23])[CH:19]=[N:18]1)=[N:5][S:6]([C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)(=[O:8])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178464671HCID 178464671, compound

Product 1

HCID 178464669HCID 178464669, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 20 mL DCM, 0.28 g N-[Ethylamino-(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methylene]-4-methoxy-benzenesulfonamide was dissolved, and 3.32 mL of a 1M solution of BBr3 in DCM was added. The mixture was stirred overnight at room temperature, extracted with 5% aqueous NaHCO3, dried over MgSO4 and evaporated to dryness. The residue was purified by flash chromatography (stepwise gradient DCM→DCM/MeOH 95:5) to yield 0.186 g (59%) of N-[Ethylamino-(4-ethyl-4,5-dihydro-pyrazol-1-yl)-methylene]-4-hydroxy-benzenesulfonamide. 1H NMR (400 MHz, CDCl3) δ 0.95 (t, J=7.52 Hz, 3H), 1.13 (t, J=7.22 Hz, 3H), 1.50 (dq, J=14.20, 7.00 Hz, 1H), 1.60 (dq, J=14.22, 7.00 Hz, 1H), 3.01-3.16 (m, 1H), 3.43-3.50 (m, 2H), 3.66 (dd, J=11.44, 7.52 Hz, 1H), 4.05 (t, J=11.29 Hz, 1H), 6.80 (br.s., 1H), 6.87 (d, J=8.73 Hz, 2H), 6.91 (d, J=1.50 Hz, 1H), 7.78 (d, J=8.73 Hz, 2H) [guanidine NH invisible].

Workup

  1. extractionextracted with 5% aqueous NaHCO3
  2. dry with materialdried over MgSO4
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography (stepwise gradient DCM

Sources & evidence

ORD record
ord-3e979d2640d24c62ae599da8ad7863ef
Source dataset
uspto-grants-2015_09
Patent number
US09126942B2

Reaction notes

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