Boron tribromide → HCID 135931642, compound

HRID 1809172Notes

Reaction equation

HRID 1809172 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]3[CH:14]=[CH:15][N:16]=[C:17]([NH:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:22][CH:21]=4)[C:12]3=[N:11][CH:10]=2)=[CH:5][C:4]=1[CH3:30].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]3[CH:14]=[CH:15][N:16]=[C:17]([NH:18][CH2:19][C:20]4[CH:21]=[CH:22][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:24][CH:25]=4)[C:12]3=[N:11][CH:10]=2)=[CH:5][C:4]=1[CH3:30]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58337097HCID 58337097, compound

Product 1

HCID 135931642HCID 135931642, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{[3-(4-Methoxy-3-methyl-phenyl)-imidazo[1,2-a]pyrazin-8-ylamino]-methyl}-benzenesulfonamide (0.167 g, 0.39 mmol) in dichloromethane (5 mL) at −78° C. was added boron tribromide (3.9 ml, 3.9 mmol, 1 M solution in dichloromethane). The reaction was allowed to warm gradually to ambient temperature then quenched with saturated aqueous sodium bicarbonate solution (30 mL). The reaction mixture was extracted with ethyl acetate (3×30 ml), the organic layers were combined and dried with magnesium sulphate, filtered and concentrated in vaccuo. The residue was taken up in DMSO and purified by prep HPLC. The product, 4-{[3-(4-Hydroxy-3-methyl-phenyl)-imidazo[1,2-a]pyrazin-8-ylamino]-methyl}-benzenesulfonamide, is obtained as a white solid (25 mg, 16%) (LC-MS m/z 410 [M+H]+).

Workup

  1. customthen quenched with saturated aqueous sodium bicarbonate solution (30 mL)
  2. extractionThe reaction mixture was extracted with ethyl acetate (3×30 ml)
  3. dry with materialdried with magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vaccuo
  6. custompurified by prep HPLC

Sources & evidence

ORD record
ord-792a59f5fe6f4cbd8a107acb15c4759c
Source dataset
uspto-grants-2013_01
Patent number
US08362018B2

Reaction notes

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