Sodium hydride → HCID 58243409, compound

HRID 2361691Notes

Reaction equation

HRID 2361691 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([N:14]3[CH2:17][CH:16]([CH2:18][OH:19])[CH2:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[F-].[Cs+].Br[C:25]1[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:33])[F:32])=[N:29][CH:30]=1>CS(C)=O.ClCCl>[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([N:14]3[CH2:15][CH:16]([CH2:18][O:19][C:25]4[CH:30]=[N:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)[CH2:17]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25953Cesium fluorideHCID 27611975-Bromo-2-(trifluoromethyl)pyridineHCID 58243416HCID 58243416, compound

Product 1

HCID 58243409HCID 58243409, compoundYield 45.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of {1-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-yl}methano 1 (20 mg, 74 μmol) in DMSO (1 ml) was added NaH (6 mg of a 60% dispersion in mineral oil, 0.15 mmol). After 30 minutes CsF (12 mg, 74 μmol) and 5-bromo-2-trifluoromethylpyridine (34 mg, 0.15 mmol) were added and the mixture was heated at 85° C. for 2 hours. The reaction was cooled to room temperature, diluted with dichloromethane (20 ml), washed with water (20 ml), dried (MgSO4), filtered and concentrated at reduced pressure. The residue was purified by preparative HPLC to give the title compound (14 mg, 45%).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with water (20 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a15dda75db004cc6bc001181501dc26d
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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