Diisopropylethylamine → 6-Chloro-2H-chromene-3-carboxylic acid (3-imidazo[1,2-a]pyridin-2-yl-phenyl)-amide

HRID 240201Notes

Reaction equation

HRID 240201 reaction equation
CCN(C(C)C)C(C)C.[Cl:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[O:17][CH2:16][C:15]([C:21]([OH:23])=O)=[CH:14]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:48]1[C:49]([C:57]2[CH:58]=[C:59]([NH2:63])[CH:60]=[CH:61][CH:62]=2)=[CH:50][N:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=12>CN(C=O)C>[N:48]1[C:49]([C:57]2[CH:58]=[C:59]([NH:63][C:21]([C:15]3[CH2:16][O:17][C:18]4[C:13]([CH:14]=3)=[CH:12][C:11]([Cl:10])=[CH:20][CH:19]=4)=[O:23])[CH:60]=[CH:61][CH:62]=2)=[CH:50][N:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=12

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5969296-chloro-2H-chromene-3-carboxylic acidHCID 6970213-(Imidazo(1,2-a)pyridin-2-yl)anilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 668650416-Chloro-2H-chromene-3-carboxylic acid (3-imidazo[1,2-a]pyridin-2-yl-phenyl)-amideYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (45.5 μL, 0.26 mmol) was added to 6-chloro-2H-chromene-3-carboxylic acid (50.0 mg, 0.24 mmol) and HATU (99.3 mg, 0.26 mmol) in 2 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-Imidazo[1,2-a]pyridin-2-yl-phenylamine (49.7 mg, 0.24 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 66.6 mg of product in 69% yield: LCMS (ESI) m/z 401 (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-bcbcc6862ee0441c97b03354fbae9869
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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