Triethylamine → Methyl 4-(4-(3-(6-methylpyridin-3-yl)ureido)-2,3-dihydro-1H-inden-1-yl)piperazine-1-carboxylate

HRID 241801Notes

Reaction equation

HRID 241801 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12]1.C(N(CC)CC)C.[CH3:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]=[C:36]=[O:37])=[CH:31][N:30]=1>C(Cl)Cl>[CH3:28][C:29]1[N:30]=[CH:31][C:32]([NH:35][C:36](=[O:37])[NH:1][C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][CH2:5][CH:6]3[N:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:15][CH2:16]2)=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 73305055-Isocyanato-2-methylpyridineHCID 59302728methyl 4-(4-amino-2,3-dihydro-1H-inden-1-yl)piperazine-1-carboxylate

Product 1

HCID 11560576Methyl 4-(4-(3-(6-methylpyridin-3-yl)ureido)-2,3-dihydro-1H-inden-1-yl)piperazine-1-carboxylateYield 51.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a room temperature solution of Methyl 4-(4-amino-2,3-dihydro-1H-inden-1-yl)piperazine-1-carboxylate (175 mg, 0.635 mmol, 1.0 equiv) and triethylamine (90 μL, 0.635 mmol, 1.0 equiv) in dry DCM (1.7 mL) was added freshly filtered 2-methyl-5-isocyanatopyridine (94 mg, 0.699 mmol, 1.1 equiv) in dry DCM (1.7 mL) dropwise via cannula. After 1 h, the reaction was diluted with DCM and washed with water and with brine. The resulting solution was dried over sodium sulfate, filtered, and concentrated in vacuo. The solid was dissolved in a minimal volume of DMF and water was added to precipitate the product. The resulting solid was filtered, washed three times with water and twice with hexane to provide the title compound as a light brown solid (133 mg, 51%). LCMS [M+H]+=410.1.

Workup

  1. washwashed with water and with brine
  2. dry with materialThe resulting solution was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe solid was dissolved in a minimal volume of DMF and water
  6. additionwas added
  7. customto precipitate the product
  8. filtrationThe resulting solid was filtered
  9. washwashed three times with water

Sources & evidence

ORD record
ord-076df6573c714e2f8257cf5440d5329f
Source dataset
uspto-grants-2014_02
Patent number
US08653081B2

Reaction notes

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