Sodium hydride → HCID 67057850, compound

HRID 2361706Notes

Reaction equation

HRID 2361706 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([CH:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:10][CH2:9]2)=[O:7])[CH2:3]1.Cl[C:26]1[CH:31]=[CH:30][N:29]=[C:28]([CH3:32])[CH:27]=1.[H-].[Na+]>CS(C)=O.CCOC(C)=O>[CH3:32][C:28]1[N:29]=[CH:30][C:31]([O:1][CH:2]2[CH2:3][N:4]([C:6]([CH:8]3[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[O:16])[CH2:10][CH2:9]3)=[O:7])[CH2:5]2)=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 5813924-Chloro-2-methylpyridineHCID 67057865HCID 67057865, compound

Product 1

HCID 67057850HCID 67057850, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of benzyl 4-[(3-hydroxyazetidin-1-yl)carbonyl]azepane-1-carboxylate (97 mg, 0.29 mmol) and 4-chloro-2-methylpyridine (52 μl, 0.46 mmol) in DMSO (2 ml) was added NaH (37 mg of a 60% dispersion in mineral oil, 0.93 mmol). The mixture was stirred at room temperature for 12 hours, 50° C. for 3 hours and a further 12 hours at room temperature. The reaction was then diluted with EtOAc (20 ml) and washed with water (3×10 ml), dried (MgSO4), filtered and concentrated. The residue was purified by silica FCC (using a gradient of eluents; 99:1:1 to 95:5:1 DCM/MeOH/2M NH3 in MeOH) to give the title product as colourless oil (35 mg, 29%).

Workup

  1. washwashed with water (3×10 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica FCC (

Sources & evidence

ORD record
ord-99fcdd3b1c5b4e68a8c030d8fb5daf57
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

Loading…