Sodium hydride → HCID 178481545, compound

HRID 707267Notes

Reaction equation

HRID 707267 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:15])[NH:9][C@H:10]1[CH2:13][C@H:12]([OH:14])[CH2:11]1)([CH3:6])([CH3:5])[CH3:4].Cl[C:17]1[N:21]([CH3:22])[C:20]2[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=2[N:18]=1>CN(C=O)C.O>[C:3]([O:7][C:8](=[O:15])[NH:9][C@H:10]1[CH2:13][C@H:12]([O:14][C:17]2[N:21]([CH3:22])[C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[N:18]=2)[CH2:11]1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 6630802-chloro-1-methyl-1H-1,3-benzodiazoleHCID 178454126HCID 178454126, compound

Product 1

HCID 178481545HCID 178481545, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride, 60% in oil (0.141 mL, 6.70 mmol) was added portionwise to a solution of tert-butyl(trans-3-hydroxycyclobutyl)carbamate (0.57 g, 3.04 mmol) and 2-chloro-1-methyl-1H-benzoimidazole (0.558 g, 3.35 mmol) in DMF (3 mL). The reaction mixture was stirred at room temperature for 3 h, diluted with water and extracted with EtOAc. EtOAc extract was concentrated and residue purified with ISCO eluting with 0-40% EtOAc/hexanes to give the desired product tert-butyl(trans-3-((1-methyl-1H-benzo[d]imidazol-2-yl)oxy)cyclobutyl)carbamate (0.388 g, 1.222 mmol, 40.2% yield). m/z: 318.2 (M+1)

Workup

  1. extractionextracted with EtOAc
  2. extractionEtOAc extract
  3. concentrationwas concentrated
  4. customresidue purified with ISCO
  5. washeluting with 0-40% EtOAc/hexanes

Sources & evidence

ORD record
ord-c843cf77cc6848e998e0b4f17f354054
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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