tert-Butanol → HCID 59129739, compound
Reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[N:7][C:8]([CH3:15])=[C:9]([CH2:13][CH3:14])[C:10]=2[CH3:12])[S:5][C:4]=1C(O)=O)#[N:2].C([N:21]([CH2:24]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.[C:43]([OH:47])([CH3:46])([CH3:45])[CH3:44]>>[C:43]([O:47][C:24](=[O:33])[NH:21][C:4]1[S:5][C:6]2=[N:7][C:8]([CH3:15])=[C:9]([CH2:13][CH3:14])[C:10]([CH3:12])=[C:11]2[C:3]=1[C:1]#[N:2])([CH3:46])([CH3:45])[CH3:44]Participants
5
Conditions
- Temperature
- 80 °C
Procedure
3-Cyano-5-ethyl-4,6-dimethylthieno[2,3-b]pyridine-2-carboxylic acid (1.00 g, 3.85 mmol) was mixed with triethylamine (0.78 g, 1.07 mL, 7.69 mmol), diphenylphosphoryl azide (2.12 g, 7.69 mmol) and anhydrous t-butanol (15 mL). The mixture was stirred at 80° C. for 8 h, followed by the removal of the volatiles under vacuum. To the residue was added dichloromethane (150 mL) and saturated NaHCO3 (40 mL), and the mixture was filtered after stirring at room temperature for 0.5 h. The organics were separated from the filtrate and dried over anhydrous Na2SO4. After removal of the solvent, the residue was chromatographed to give (3-cyano-5-ethyl-4,6-dimethyl-thieno[2,3-b]pyridin-2-yl)-carbamic acid tert-butyl ester. MS (ES+) m/z: 332.
Workup
- customfollowed by the removal of the volatiles under vacuum
- additionTo the residue was added dichloromethane (150 mL) and saturated NaHCO3 (40 mL)
- filtrationthe mixture was filtered
- stirringafter stirring at room temperature for 0.5 h
- customThe organics were separated from the filtrate
- dry with materialdried over anhydrous Na2SO4
- customAfter removal of the solvent
- customthe residue was chromatographed
Sources & evidence
- ORD record
- ord-2f6cbce8f8b94d699f4439d868a5b373
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07645881B2
Reaction notes
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