Diisopropylethylamine → HCID 44197382, compound

HRID 240039

Reaction equation

HRID 240039 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[O:18][C:17](=[O:22])[C:16]([C:23]([OH:25])=O)=[CH:15]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:50]1[C:51]([C:59]2[CH:60]=[C:61]([NH2:65])[CH:62]=[CH:63][CH:64]=2)=[CH:52][N:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=12>CN(C=O)C>[N:50]1[C:51]([C:59]2[CH:60]=[C:61]([NH:65][C:23]([C:16]3[C:17](=[O:22])[O:18][C:19]4[C:14]([CH:15]=3)=[CH:13][C:12]([O:11][CH3:10])=[CH:21][CH:20]=4)=[O:25])[CH:62]=[CH:63][CH:64]=2)=[CH:52][N:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=12

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6970213-(Imidazo(1,2-a)pyridin-2-yl)anilineHCID 7117176-methoxy-2-oxo-2H-chromene-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 44197382HCID 44197382, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (43.5 μL, 0.25 mmol) was added to 6-methoxy-3-carboxy-coumarin (50.0 mg, 0.23 mmol) and HATU (95.0 mg, 0.25 mmol) in 1 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-Imidazo[1,2-a]pyridin-2-yl-phenylamine (475. mg, 0.23 mmol) was added and allowed to react overnight when a solid precipitated out of solution. The resulting precipitate was filtered, dried under suction, and finally dried overnight in vacuo to give 78.5 mg of product in 83% yield: LCMS (ESI) m/z 412 (MH+).

Workup

  1. customresulted
  2. customto react overnight when a solid
  3. customprecipitated out of solution
  4. filtrationThe resulting precipitate was filtered
  5. customdried under suction, and finally dried overnight in vacuo

Sources & evidence

ORD record
ord-910c7c2cc0814008822277171030d6d4
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Linked notes

Loading…