Imidazole → HCID 86727103, compound

HRID 2175911Notes

Reaction equation

HRID 2175911 reaction equation
[CH3:1][C:2]([CH3:24])([CH3:23])[C:3]([NH:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:8]([CH2:20][CH2:21]O)[CH:7]=1)=[O:4].N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:50]>ClCCl.O>[C:16]([O:15][C:13](=[O:14])[CH2:12][C:9]1[CH:10]=[N:11][C:6]([NH:5][C:3](=[O:4])[C:2]([CH3:24])([CH3:23])[CH3:1])=[CH:7][C:8]=1[CH2:20][CH2:21][Br:50])([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 131732969HCID 131732969, compound

Product 1

HCID 86727103HCID 86727103, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl {6-[(2,2-dimethylpropanoyl)amino]-4-(2-hydroxyethyl)pyridin-3-yl}acetate (2.30 g, 6.84 mmol) with imidazole (0.558 g, 8.20 mmol) in dichloromethane (50 mL) was treated with triphenylphosphine (1.79 g, 6.84 mmol) and carbon tetrabromide (2.72 g, 8.20 mmol). The reaction mixture was allowed to stir at room temperature for 2 h, then was diluted with water and the layers separated. The organic layer was washed successively with 5% hydrochloric acid, saturated sodium bicarbonate solution, and brine, then dried (Na2SO4), filtered and concentrated. The residue was filtered through a short silica plug (20% EtOAc:hexanes eluent) to afford the title compound which was used immediately in the next step: LC/MS (M+1)+=398.9.

Workup

  1. customthe layers separated
  2. washThe organic layer was washed successively with 5% hydrochloric acid, saturated sodium bicarbonate solution, and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationThe residue was filtered through a short silica plug (20% EtOAc:hexanes eluent)

Sources & evidence

ORD record
ord-fd04c36783cb404280d8ce373de3329e
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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