Diisopropylethylamine → 7-Methoxy-2-oxo-2H-chromene-3-carboxylic acid (3-imidazo[1,2-a]pyridin-2-yl-phenyl)-amide

HRID 240013Notes

Reaction equation

HRID 240013 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][O:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[C:17]([C:23]([OH:25])=O)[C:18](=[O:22])[O:19]2)=[CH:14][CH:13]=1.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)C=O>[N:50]1[C:51]([C:59]2[CH:60]=[C:61]([NH:65][C:23]([C:17]3[C:18](=[O:22])[O:19][C:20]4[C:15]([CH:16]=3)=[CH:14][CH:13]=[C:12]([O:11][CH3:10])[CH:21]=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 5839417-Methoxycoumarin-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 866503597-Methoxy-2-oxo-2H-chromene-3-carboxylic acid (3-imidazo[1,2-a]pyridin-2-yl-phenyl)-amideYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (0.027 mL, 0.16 mmol) was added to 7-methoxy-3-carboxy-coumarin (0.031 g, 0.14 mmol) and HATU (0.060 g, 0.16 mmol) in 2 mL of dimethylformamide (DMF) with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-Imidazo[1,2-a]pyridin-2-yl-phenylamine (0.030 g, 0.14 mmol) was added and allowed to react for approximately 30 minutes, when a yellow solid precipitated out of solution. The precipitate was filtered and dried under suction and then in vacuo to give 0.051 g of 1541C in an 86% yield: 1H NMR (400 MHz, CD3OD/CDCl3) δ 10.95 (s, 1H), 8.96 (s, 1H), 8.23 (dd, J=1.8, 1.9 Hz, 1H), 8.20 (d, J=7.1 Hz, 1H), 7.99 (s, 1H), 7.79 (d, J=7.7 Hz, 1H), 7.75 (d, J=8.1 Hz, 1H), 7.68 (d, J=8.6 Hz, 1H), 7.63 (d, J=9.1 Hz, 1H), 7.48 (dd, J=7.9, 8.0 Hz, 1H), 7.25 (dd, J=5.5, 6.8 Hz, 1H), 7.01 (dd, J=2.4, 8.8 Hz, 1H), 6.95 (d, J=2.4 Hz, 1H), 6.85 (dd, J=7.0, 7.3 Hz, 1H), 3.96 (s, 3H); LCMS (ESI) m/z 412 (MH+).

Workup

  1. customresulted
  2. customto react for approximately 30 minutes
  3. customwhen a yellow solid precipitated out of solution
  4. filtrationThe precipitate was filtered
  5. customdried under suction

Sources & evidence

ORD record
ord-7519b2f7b8e14758b5feb1a2d49b45e8
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

Loading…