Bromine → HCID 20755365, compound

HRID 22877Notes

Reaction equation

HRID 22877 reaction equation
[C:1]([O:5][C:6](=[O:25])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH2:24])(=[O:17])=[O:16])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[Br:26]Br>C(O)(=O)C>[C:1]([O:5][C:6](=[O:25])[C:7]1[CH:8]=[CH:9][C:10]([CH2:13][NH:14][S:15]([C:18]2[CH:23]=[C:22]([Br:26])[CH:21]=[CH:20][C:19]=2[NH2:24])(=[O:17])=[O:16])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 207553664-[(2-Amino-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester

Product 1

HCID 20755365HCID 20755365, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

4-[(2-Amino-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester (12.16 g, 33.5 mmol) was dissolved in 150 mL of acetic acid at 10° C. A solution of bromine (2.06 mL, 40.2 mmol) in 50 mL acetic acid was added dropwise. After complete addition, a thick yellow precipitate was observed. The reaction was filtered, and the solid washed with water. Chromatography of the solid (20% ethyl acetate/hexanes, SiO2) gave 5.72 g (39%) of 4-[(2-Amino-5-bromo-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester as a white solid. 1H-NMR (CDCl3); 7.86 (d, 2H), 7.74 (d, 1H), 7.37 (dd, 1H), 7.23 (m, 2H), 6.65 (d, 1H), 5.19 (bt, 1H), 4.14 (d, 2H), and 1.58 (s, 9H). MS: M+=441.0 Da Step (4): Synthesis of 4-(7-Bromo-1,1,3-trioxo-3,4-dihydro-1H-1λ6-benzo[1,2,4]thiadiazin-2-ylmethyl)-benzoic acid tert-butyl ester

Workup

  1. additionAfter complete addition
  2. filtrationThe reaction was filtered
  3. washthe solid washed with water

Sources & evidence

ORD record
ord-e5f7f19f24964b27bdb30f5c26e9b888
Source dataset
uspto-grants-2005_02
Patent number
US06849648B2

Reaction notes

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