Sodium hydride → HCID 57379346, compound

HRID 537844Notes

Reaction equation

HRID 537844 reaction equation
Cl.[CH3:2][S:3]([N:6]1[C:14]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH:8][C:7]1=[O:15])(=[O:5])=[O:4].[H-].[Na+].Cl.[Cl:19][C:20]1[CH:35]=[CH:34][C:23]2[N:24]([CH2:29][CH2:30][CH2:31][CH2:32][F:33])[C:25]([CH2:27]Cl)=[N:26][C:22]=2[CH:21]=1>CN(C=O)C.O>[Cl:19][C:20]1[CH:35]=[CH:34][C:23]2[N:24]([CH2:29][CH2:30][CH2:31][CH2:32][F:33])[C:25]([CH2:27][N:8]3[C:9]4[CH:10]=[N:11][CH:12]=[CH:13][C:14]=4[N:6]([S:3]([CH3:2])(=[O:5])=[O:4])[C:7]3=[O:15])=[N:26][C:22]=2[CH:21]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 67975635HCID 67975635, compoundHCID 86698371HCID 86698371, compound

Product 1

HCID 57379346HCID 57379346, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1-(methylsulfonyl)-1H-imidazo[4,5-c]pyridin-2(3H)-one hydrochloride 10 (720 mg, 2.626 mmoles) in 10 mL of extra dry DMF was added sodium hydride (210 mg, 5.253 mmoles, 60% dispersion in oil) portionwise at room temperature. After 20 minutes, a solution of 5-chloro-2-(chloromethyl)-1-(4-fluorobutyl)-1H-benzo[d]imidazole hydrochloride 9 (440 mg, 1.313 mmoles) in 5 mL of DMF was added dropwise. Stirring was continued overnight at room temperature. The reaction mixture was then diluted with water (50 mL) and extracted with EtOAc (2×50 mL). The organic layers were combined, washed with brine, dried over MgSO4, filtered and concentrated under vacuum. The resulting slightly orange oil was triturated in DCM and the precipitate was filtered off. It was further washed with DCM, then isopropylether and dried under high vacuum, to provide the title product 3-((5-chloro-1-(4-fluorobutyl)-1H-benzo[d]imidazol-2-yl)methyl)-1-(methylsulfonyl)-1H-imidazo[4,5-c]pyridin-2(3H)-one P34 as a white solid in 40% yield; m/z=452 (M+H)+.

Workup

  1. waitwas continued overnight at room temperature
  2. extractionextracted with EtOAc (2×50 mL)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe resulting slightly orange oil was triturated in DCM
  8. filtrationthe precipitate was filtered off
  9. washIt was further washed with DCM
  10. dry with materialisopropylether and dried under high vacuum

Sources & evidence

ORD record
ord-8364c9d688b04276a9446d7d24ce19a0
Source dataset
uspto-grants-2014_10
Patent number
US08865705B2

Reaction notes

Loading…