Triethylamine → (S,S)-5-[4-(Benzothiazol-2-yloxy)-benzyl]-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid amide
Reaction equation
Cl.[C@H:2]12[CH2:8][C@H:5]([NH:6][CH2:7]1)[CH2:4][N:3]2[CH2:9][C:10]1[CH:25]=[CH:24][C:13]([O:14][C:15]2[S:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)=[CH:12][CH:11]=1.CCN(CC)CC.C[Si]([N:37]=[C:38]=[O:39])(C)C>C(Cl)Cl>[S:16]1[C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=[C:15]1[O:14][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:3]2[CH2:4][C@@H:5]3[CH2:8][C@H:2]2[CH2:7][N:6]3[C:38]([NH2:37])=[O:39])=[CH:25][CH:24]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred suspension of (S,S)-2-[4-(2,5-diaza-bicyclo[2.2.1]hept-2-ylmethyl)-phenoxy]-benzothiazole hydrochloride (2.8 g, 6.8 mmol) and Et3N (9.1 mL, 68.5 mmol) in CH2Cl2 (50 mL) was added trimethylsilylisocyanate (3.8 mL, 27.4 mmol), and the resulting solution was stirred at rt for 1.5 h. The solution was then partitioned between CH2Cl2 (500 mL) and satd. aq. NaHCO3 (80 mL). The organic layer was separated, dried (Na2SO4), filtered and concentrated. Purification by silica gel flash chromatography (5% to 10% CH3OH in CH2Cl2) afforded the title compound as a white solid (2.2 g, 85%).
Workup
- customThe solution was then partitioned between CH2Cl2 (500 mL)
- customThe organic layer was separated
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customPurification by silica gel flash chromatography (5% to 10% CH3OH in CH2Cl2)
Sources & evidence
- ORD record
- ord-8797af527d024a11a2efc9fd50f262b0
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344008B2
Reaction notes
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