Cesium carbonate → HCID 58333625, compound

HRID 2066842Notes

Reaction equation

HRID 2066842 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=[N:7][O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH2:3][CH2:2]1.Br[C:22]1[C:23]([CH3:28])=[N:24][CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(CN1P2N(CC(C)C)CCN(CCN2CC(C)C)CC1)C>C1(C)C=CC=CC=1>[CH3:28][C:23]1[C:22]([N:1]2[CH2:2][CH2:3][C:4](=[N:7][O:8][CH:9]3[CH2:10][CH2:11][N:12]([C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]3)[CH2:5][CH2:6]2)=[CH:27][CH:26]=[CH:25][N:24]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 12010033-Bromo-2-methylpyridineHCID 45712432,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecaneHCID 57461147Isopropyl 4-(Piperidin-4-ylideneaminooxy)piperidine-1-carboxylate

Product 1

HCID 58333625HCID 58333625, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Compound 2d (30 mg, 0.11 mmol), 3-bromo-2-methyl-pyridine (0.16 mmol), cesium carbonate (72 mg, 0.22 mmol), PddppfCl2 (10 mg), and triisobutylphosphatrane (15 μL) were combined in toluene (0.5 mL). The mixture was heated at 80° C. for 20 h. The mixture was concentrated under a stream of nitrogen and the residue was partitioned between DCM and water. The DCM layer was concentrated and taken up in methanol and purified by preparative HPLC to afford 4-1: LC-MS 375.4 (MH+), tR=7.88 (Method 6). EC50: 4804 nM.

Workup

  1. concentrationThe mixture was concentrated under a stream of nitrogen
  2. customthe residue was partitioned between DCM and water
  3. concentrationThe DCM layer was concentrated
  4. custompurified by preparative HPLC
  5. customto afford 4-1

Sources & evidence

ORD record
ord-77df762277ba40d7954e3110e124e443
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

Loading…