2,6-Lutidine → HCID 136381450, compound
Reaction equation
C([O:3][P:4]([CH:9]=[CH:10][CH:11]1[CH:15]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]([O:25][CH3:26])[CH:13]([N:27]2[CH:35]=[N:34][C:33]3[C:32](=[O:36])[NH:31][C:30]([NH:37][C:38](=[O:42])[CH:39]([CH3:41])[CH3:40])=[N:29][C:28]2=3)[O:12]1)([O:6]CC)=[O:5])C.N1C(C)=CC=CC=1C.C[Si](Br)(C)C>CN(C=O)C>[C:38]([NH:37][C:30]1[NH:31][C:32](=[O:36])[C:33]2[N:34]=[CH:35][N:27]([CH:13]3[O:12][CH:11]([CH:10]=[CH:9][P:4]([OH:5])([OH:6])=[O:3])[CH:15]([O:16][C:17](=[O:24])[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:14]3[O:25][CH3:26])[C:28]=2[N:29]=1)(=[O:42])[CH:39]([CH3:40])[CH3:41]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Compound 16.7 (460 mg, 0.763 mmol) was dissolved in 8 mL anhydrous DMF, treated with 2,6-lutidine (0.443 mL, 3.81 mmol) and TMSBr (1.5 mL, 11.4 mmol). The mixture was stirred at 80° C. for 4 h and quenched with MeOH. The mixture was concentrated under reduced pressure and the residue was subjected to reverse phase HPLC to yield product 16.8 (60 mg, 14.4% yield).
Workup
- customquenched with MeOH
- concentrationThe mixture was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-dd5db4607e3f45f68d76c1b96836e5f4
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324179B2
Reaction notes
Loading…