Bromine → HCID 59262675, compound

HRID 908347Notes

Reaction equation

HRID 908347 reaction equation
O[C:2]1[C:11]2[N:10]=[C:9]([NH:12][C:13]3[CH:14]=[C:15]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=3)[N:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH:3]=1.BrBr.[C:25]([NH2:28])(=[S:27])[CH3:26]>C(Cl)(Cl)Cl.C(O)C>[CH3:26][C:25]1[S:27][C:3]2[CH2:4][CH2:5][C:6]3[C:11](=[N:10][C:9]([NH:12][C:13]4[CH:14]=[C:15]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=4)=[N:8][CH:7]=3)[C:2]=2[N:28]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 2723949ThioacetamideHCID 59262782HCID 59262782, compound

Product 1

HCID 59262675HCID 59262675, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of 3-(8-hydroxy-5,6-dihydro-quinazolin-2-ylamino)benzenesulfonamide (100 mg, 0.314 mmol) in chloroform (1 mL) was treated with a solution of bromine (32 μl, 0.628 mmol) in chloroform (1 mL) and the mixture stirred at room temperature for 2 hours giving an insoluble black residue. The solvent was decanted and the residue treated with thioacetamide (47 mg, 0.6 mmol) in ethanol (3 mL). The mixture was stirred at 80° C. for 3 hours and filtered to give a black solid (75 mg). The solid was dissolved in DMSO and purified by reverse phase preparative HPLC [Waters Delta-Pak C18, 15 uM, 100 A column, gradient 10%-100% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 10 minutes at 25 mL/min] to give a yellow solid (6.9 mg) which was further purified by flash chromatography on silica gel eluting with ethyl acetate to afford the title compound (1.9 mg) as a pale yellow solid. MS (ES+) 374, (ES−) 372. δH (CD3OD) 2.78 (3H, s), 3.01-3.07 (2H, m), 3.10-3.16 (2H, m), 7.46 (1H, t), 7.53 (1H, d), 7.65 (2H, s, partially exchanged), 7.83 (1H, d), 8.27 (1H, s), 8.48 (1H, s).

Workup

  1. customgiving an insoluble black residue
  2. customThe solvent was decanted
  3. stirringThe mixture was stirred at 80° C. for 3 hours
  4. filtrationfiltered

Sources & evidence

ORD record
ord-f797bfee26394c48a32bbfc6e063cdbc
Source dataset
uspto-grants-2011_09
Patent number
US08017619B2

Reaction notes

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