Water → HCID 86684894, compound

HRID 1530263Notes

Reaction equation

HRID 1530263 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-7f65da0436944dda95443bb629a4ed6a
Source dataset
uspto-grants-2015_07
Patent number
US09090562B2

Reaction notes

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