Water → HCID 86684894, compound

HRID 1616424Notes

Reaction equation

HRID 1616424 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12](=[O:37])[C:13]1[CH:18]=[C:17]([C:19]2[CH:20]=[N:21][C:22]([CH2:25]O)=[CH:23][CH:24]=2)[CH:16]=[C:15]([N:27]([CH2:34][CH3:35])[CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[C:14]=1[CH3:36].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:58].O>C(Cl)Cl>[Br:58][CH2:25][C:22]1[N:21]=[CH:20][C:19]([C:17]2[CH:16]=[C:15]([N:27]([CH2:34][CH3:35])[CH:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[C:14]([CH3:36])=[C:13]([CH:18]=2)[C:12]([NH:11][CH2:10][C:3]2[C:4](=[O:9])[NH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])=[O:37])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 70872699HCID 70872699, compound

Product 1

HCID 86684894HCID 86684894, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-5-(6-(hydroxymethyl)pyridin-3-yl)-2-methylbenzamide (0.35 g, 0.694 mmol) in DCM (5 mL), triphenyl phosphine (0.361 g, 1.38 mmol) was added and stirred it at room temperature for 10 min. Finally CBr4 (0.318 g, 1.38 mmol) was added portion wise to it and resulting solution was stirred at room temperature for 18 h. On completion, water was added to the reaction mass and extraction was carried out using DCM. Combined organic layers were dried over sodium sulphate, concentrated under reduced pressure to give crude material which then column purification gave desired compound (0.35 g, 89%).

Workup

  1. customresulting solution
  2. stirringwas stirred at room temperature for 18 h
  3. dry with materialCombined organic layers were dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto give crude material which
  6. customcolumn purification

Sources & evidence

ORD record
ord-3ded4464b0d84dc3a1a49410995493eb
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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