Triethylamine → HCID 178454122, compound

HRID 707293Notes

Reaction equation

HRID 707293 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]1[CH2:11][C@H:10]([NH2:12])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[C:16]([C:21]([CH3:26])([CH3:25])[C:22](O)=[O:23])=[N:17][CH:18]=[CH:19][N:20]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(Cl)Cl.O>[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]1[CH2:11][C@H:10]([NH:12][C:22](=[O:23])[C:21]([C:16]2[C:15]([Cl:14])=[N:20][CH:19]=[CH:18][N:17]=2)([CH3:26])[CH3:25])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866941182-(3-Chloropyrazin-2-yl)-2-methylpropanoic acidHCID 178454111HCID 178454111, compound

Product 1

HCID 178454122HCID 178454122, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a round bottomed flask was added tert-butyl(trans-3-aminocyclobutyl)carbamate (1.847 g, 9.92 mmol), 2-(3-chloropyrazin-2-yl)-2-methylpropanoic acid (1.99 g, 9.92 mmol), HATU (4.90 g, 12.89 mmol), and triethylamine (5.52 ml, 39.7 mmol) in DCM (25 ml) to stir at room temperature for 16 h. The reaction mixture was diluted with water and extracted with CH2Cl2. The organic extract was washed with water, saturated NaCl solution, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 10% to 70% EtOAc in hexane, to provide the title compound (2.73 g, 7.40 mmol, 74.6% yield) as off-white solid.

Workup

  1. extractionextracted with CH2Cl2
  2. extractionThe organic extract
  3. washwas washed with water, saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g)
  8. washeluting with a gradient of 10% to 70% EtOAc in hexane

Sources & evidence

ORD record
ord-c5495091722d4a97b3bf008a8caca66e
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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