Hydrogen Bromide → HCID 86649130, compound
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C@@H:15]([C:16](=O)[CH:17]=[N+]=[N-])[CH2:14][CH2:13][C@@H:12]2C(=O)C=[N+]=[N-])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Br.O.[NH2:28][C:29]([NH2:31])=[S:30].CCO[CH2:35][CH3:36]>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C@@H:15]([C:16]3[N:28]=[C:29]([NH2:31])[S:30][CH:17]=3)[CH2:14][CH2:13][C@@H:12]2[C:35]2[N:28]=[C:29]([NH2:31])[S:30][CH:36]=2)=[CH:7][CH:6]=1)([CH3:2])([CH3:4])[CH3:3]Participants
Procedure
A solution of the product from Example 214D (0.50 g, 1.47 mmol) in Et2O (10 mL) was treated dropwise with 48% aq. hydrogen bromide (0.500 mL, 4.42 mmol). The resulting mixture was stirred at rt for 30 min. Water (1 mL) was added, and the mixture was extracted with Et2O (3×10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was dissolved in EtOH (15 mL). To the resulting solution was added thiourea (0.45 g, 5.89 mmol), and the resulting mixture was stirred at rt for 1 h and then concentrated to ca. 1 mL. Water (10 mL) was added, and the pH was neutralized using saturated aq. NaHCO3. The resulting solid was collected by filtration and dried in vacuo to give the title compound (0.455 g, 77%).
Workup
- extractionthe mixture was extracted with Et2O (3×10 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- dissolutionThe residue was dissolved in EtOH (15 mL)
- stirringthe resulting mixture was stirred at rt for 1 h
- concentrationconcentrated to ca. 1 mL
- additionWater (10 mL) was added
- filtrationThe resulting solid was collected by filtration
- customdried in vacuo
Sources & evidence
- ORD record
- ord-f4b3a7320418490598e3ec6aaa5c2367
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691938B2
Reaction notes
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