Boron tribromide → HCID 178464670, compound

HRID 1396041Notes

Reaction equation

HRID 1396041 reaction equation
[CH2:1]([NH:3][C:4]([N:17]1[CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20][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[CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20][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 178464672HCID 178464672, compound

Product 1

HCID 178464670HCID 178464670, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under N2 atmosphere, to a solution of 1.05 g N-[ethylamino-(5-phenyl-4,5-dihydro-pyrazol-1-yl)-methylene]-4-methoxy-benzenesulfonamide in 25 mL DCM, 12.91 mL of a 1M solution of boron tribromide in DCM was added. The mixture was stirred overnight at room temperature under N2 atmosphere, quenched with water, and stirred for another 30 minutes. The solids were filtered off and the filtrate was extracted with water. The organic layer was dried over MgSO4 and evaporated to dryness. The residue was purified by flash chromatography (stepwise gradient DCM→DCM/MeOH 95:5). The pure fractions were concentrated and triturated with Et2O. The solids were filtered off and dried in vacuo to give 0.34 g (34%) of N-[ethylamino-(5-phenyl-4,5-dihydro-pyrazol-1-yl)-methylene]-4-hydroxy-benzenesulfonamide as a grey crystalline material, m.p. 158-160° C. 1H NMR (400 MHz, DMSO-d6) δ 1.07 (t, J=7.2 Hz, 3H), 2.69-2.81 (m, 1H), 3.36-3.47 (m, 1H), 3.49-3.59 (m, 2H), 5.40-5.51 (m, 1H), 6.55 (d, J=8.7 Hz, 2H), 7.00 (d, J=8.4 Hz, 2H), 7.04-7.12 (m, 3H), 7.22-7.29 (m, 3H), 9.71 (s, 1H) [guanidine NH invisible].

Workup

  1. customquenched with water
  2. stirringstirred for another 30 minutes
  3. filtrationThe solids were filtered off
  4. extractionthe filtrate was extracted with water
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography (stepwise gradient DCM
  8. concentrationThe pure fractions were concentrated
  9. customtriturated with Et2O
  10. filtrationThe solids were filtered off
  11. customdried in vacuo

Sources & evidence

ORD record
ord-745a45da69fc4815a551a6b37edbcbfe
Source dataset
uspto-grants-2014_12
Patent number
US08901108B2

Reaction notes

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