Diisopropylethylamine → N-(3-(imidazo[1,2-a]pyridin-2-yl)phenyl)-7-methoxybenzofuran-2-carboxamide

HRID 240200Notes

Reaction equation

HRID 240200 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][O:11][C:12]1[C:20]2[O:19][C:18]([C:21]([OH:23])=O)=[CH:17][C:16]=2[CH:15]=[CH:14][CH:13]=1.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:18]3[O:19][C:20]4[C:12]([O:11][CH3:10])=[CH:13][CH:14]=[CH:15][C:16]=4[CH:17]=3)=[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 6060377-Methoxy-1-benzofuran-2-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 44197655N-(3-(imidazo[1,2-a]pyridin-2-yl)phenyl)-7-methoxybenzofuran-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (49.9 μL, 0.29 mmol) was added to 7-Methoxy-benzofuran-2-carboxylic acid (50 mg, 0.26 mmol) and HATU (108.8 mg, 0.29 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 (54.4 mg, 0.26 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 the final product: LCMS (ESI) m/z 384 (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-c846c3de17664be0922ac4d1ec39d2d2
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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