Diisopropylethylamine → HCID 57898919, compound

HRID 911068Notes

Reaction equation

HRID 911068 reaction equation
[Br:1][C:2]1[C:3]([CH2:22][C:23]([OH:25])=O)=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]=2)=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.CN(C)C(F)=[N+](C)C.O[NH:51][C:52](=[NH:54])[CH3:53]>CN(C=O)C.ClCCl>[Br:1][C:2]1[C:3]([CH2:22][C:23]2[O:25][N:54]=[C:52]([CH3:53])[N:51]=2)=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:13]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphateHCID 86634782HCID 86634782, compoundHCID 178465666HCID 178465666, compound

Product 1

HCID 57898919HCID 57898919, compoundYield 11.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A vial was charged with 2-(5-bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-yl)acetic acid (0.0863 g, 0.2063 mmol) in 5 ml of DMF and DIEA (0.03953 ml, 0.2269 mmol), and tetramethylfluoroformamidinium hexafluorophosphate (TFFH) (0.060 g, 0.227 mmol) were added consecutively. The mixture was stirred for 30 minutes and N-hydroxyacetamidine (0.0168 g, 0.227 mmol) was added. The mixture was heated at 100° C. overnight. The mixture was then cooled, diluted with dichloromethane, and washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography, eluting with 20% ethyl acetate/hexane to provide N-(5-bromo-4-((3-methyl-1,2,4-oxadiazol-5-yl)methyl)pyridin-2-yl)-4-phenethylthiazol-2-amine (11 mg, 11.58% yield) as a yellow solid. 1H NMR (CDCl3) δ 2.37 (s, 3H), 2.94-2.98 (m, 4H), 4.25 (s, 2H), 6.39 (s, 1H), 6.89 (s, 1H), 7.14-7.26 (m, 5H), 8.45 (s, 1H).

Workup

  1. additionwere added consecutively
  2. temperatureThe mixture was then cooled
  3. washwashed with aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-1b0e2cfbe2224fb4a47f7f9573cc8ff9
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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