Hydrogen Bromide → HCID 66817717, compound

HRID 1755014Notes

Reaction equation

HRID 1755014 reaction equation
Br.C([N:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([CH3:41])=[C:12]([CH2:18][CH2:19][S:20]([N:23]3[CH2:40][CH2:39][C:26]4([N:30]=[C:29]([CH:31]5[CH2:36][CH2:35][CH:34]([CH3:37])[CH2:33][CH2:32]5)[NH:28][C:27]4=[O:38])[CH2:25][CH2:24]3)(=[O:22])=[O:21])[C:13]=2[CH3:17])[NH:8][C:7]1=[O:42])(C)(C)C>C(O)(=O)C>[CH3:17][C:13]1[C:12]([CH2:18][CH2:19][S:20]([N:23]2[CH2:40][CH2:39][C:26]3([N:30]=[C:29]([CH:31]4[CH2:32][CH2:33][CH:34]([CH3:37])[CH2:35][CH2:36]4)[NH:28][C:27]3=[O:38])[CH2:25][CH2:24]2)(=[O:22])=[O:21])=[C:11]([CH3:41])[CH:10]=[C:9]2[C:14]=1[C:15](=[O:16])[NH:6][C:7](=[O:42])[NH:8]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 66818620HCID 66818620, compound

Product 1

HCID 66817717HCID 66817717, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

An aqueous hydrogen bromide solution (80 μL) was added to a mixed solution of 3-tert-butyl-5,7-dimethyl-6-{2-[2-(4-methyl-cyclohexyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-1H-quinazoline-2,4-dione (3.3 mg, 3.41 μmol) in acetic acid (80 μL), and the mixture was heated with stirring at 100° C. for one hour. The reaction solution was returned to room temperature and then concentrated under reduced pressure, and the resulting residue was purified by preparative TLC to give 5,7-dimethyl-6-{2-[2-(4-methyl-cyclohexyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-1H-quinazoline-2,4-dione as a pale yellow solid (1.2 mg, 44%).

Workup

  1. temperaturethe mixture was heated
  2. customwas returned to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customthe resulting residue was purified by preparative TLC

Sources & evidence

ORD record
ord-0ceb11e2fc644c5b9acd6fec32235e4c
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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