Triethylamine → tert-Butyl 4-((4-(3-(6-methylpyridin-3-yl)ureido)benzo[d]oxazol-2-yl)methyl)piperazine-1-carboxylate

HRID 241805Notes

Reaction equation

HRID 241805 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]=[C:40]=[O:41])=[CH:35][N:34]=1>C(Cl)Cl>[CH3:32][C:33]1[N:34]=[CH:35][C:36]([NH:39][C:40](=[O:41])[NH:1][C:2]2[C:7]3[N:8]=[C:9]([CH2:11][N:12]4[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]4)[O:10][C:6]=3[CH:5]=[CH:4][CH:3]=2)=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 73305055-Isocyanato-2-methylpyridineHCID 59302726tert-Butyl 4-((4-aminobenzo[d]oxazol-2-yl)methyl)piperazine-1-carboxylate

Product 1

HCID 23654605tert-Butyl 4-((4-(3-(6-methylpyridin-3-yl)ureido)benzo[d]oxazol-2-yl)methyl)piperazine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a room temperature solution of tert-butyl 4-((4-aminobenzo[d]oxazol-2-yl)methyl)piperazine-1-carboxylate (5.0 g, 15.1 mmol, 1.0 equiv) and triethylamine (2.1 g, 15.1 mmol, 1.0 equiv) in dry DCM (37 mL) was added 2-methyl-5-isocyanatopyridine (2.22 g, 16.6 mmol, 1.1 equiv) in dry DCM (37 mL) via cannula. After 1 h, the reaction mixture was filtered and washed with water (25 mL) and brine (25 mL). The solution was dried over sodium sulfate, filtered and concentrated in vacuo. Silica gel purification (5% MeOH/95% EtOAc—15% MeOH/85% EtOAc) provided the title compound as a white foam (7.03 g, 100%). LCMS [M+H]+=467.2.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washwashed with water (25 mL) and brine (25 mL)
  3. dry with materialThe solution was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customSilica gel purification (5% MeOH/95% EtOAc—15% MeOH/85% EtOAc)

Sources & evidence

ORD record
ord-2bc9b1d91be945c48bdeeb0cc42ebf8d
Source dataset
uspto-grants-2014_02
Patent number
US08653081B2

Reaction notes

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