Ammonia → HCID 57962540, compound
Reaction equation
[Cl:1][C:2]1[C:3]2[NH:4][C:5]3[CH:6]=[C:7]4[C:11](=[C:12]([CH:26]=3)[CH2:13][CH2:14][C:15]3[CH:25]=[C:19]([NH:20][C:21]([N:24]=2)=[N:22][CH:23]=1)[CH:18]=[CH:17][CH:16]=3)[O:10][C:9](=[O:27])[N:8]4COCC[Si](C)(C)C.N.O.C(OCC)(=O)C>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[C:3]2[NH:4][C:5]3[CH:6]=[C:7]4[C:11](=[C:12]([CH:26]=3)[CH2:13][CH2:14][C:15]3[CH:25]=[C:19]([NH:20][C:21]([N:24]=2)=[N:22][CH:23]=1)[CH:18]=[CH:17][CH:16]=3)[O:10][C:9](=[O:27])[NH:8]4Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A solution of 4-chloro-20-{[2-(trimethylsilyl)ethoxy]methyl}-18-oxa-2,6,8,20,25-pentaazapentacyclo[14.6.1.1(3,7).1(9,13).0(17,21)]pentacosa-1(23),3(25),4,6,9(24),10,12,16,21-nonaen-19-one (25 mg, 49 μmol) in TFA (1.5 mL) was stirred at 20° C. for 30 min. The reaction mixture was concentrated and reconcentrated from dichloromethane to a residue. This residue was dissolved in THF (1.5 mL) and treated with 20 M of ammonia in water (1 mL, 20 mmol) dropwise and stirred at 20° C. for 1 h. The reaction mixture was poured into water (20 mL) and ethyl acetate (50 mL). The organic layer was separated and washed with brine (10 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to give the desired product (19 mg, quantitative) as a white solid. LCMS for C19H15ClN5O2 (M+H)+: m/z=380.0.
Workup
- concentrationThe reaction mixture was concentrated
- dissolutionThis residue was dissolved in THF (1.5 mL)
- customThe organic layer was separated
- washwashed with brine (10 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-eb1c724035c34a6ba9c37156f4db089a
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871753B2
Reaction notes
Loading…