Diisopropylethylamine → 6-Methoxy-8-morpholin-4-ylmethyl-2-oxo-2H-chromene-3-carboxylic acid (3-imidazo[1,2-a]pyridin-2-yl-phenyl)-amide

HRID 240015Notes

Reaction equation

HRID 240015 reaction equation
CCN(C(C)C)C(C)C.[N:10]1([CH2:16][C:17]2[CH:18]=[C:19]([O:31][CH3:32])[CH:20]=[C:21]3[C:26]=2[O:25][C:24](=[O:27])[C:23]([C:28](O)=[O:29])=[CH:22]3)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:57]1[C:58]([C:66]2[CH:67]=[C:68]([NH2:72])[CH:69]=[CH:70][CH:71]=2)=[CH:59][N:60]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=12>CN(C)C=O>[N:57]1[C:58]([C:66]2[CH:67]=[C:68]([NH:72][C:28]([C:23]3[C:24](=[O:27])[O:25][C:26]4[C:21]([CH:22]=3)=[CH:20][C:19]([O:31][CH3:32])=[CH:18][C:17]=4[CH2:16][N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)=[O:29])[CH:69]=[CH:70][CH:71]=2)=[CH:59][N:60]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=12

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 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)HCID 866503618-(4-Morpholinylmethyl)-3-carboxy-6-methoxy-coumarin

Product 1

HCID 866503606-Methoxy-8-morpholin-4-ylmethyl-2-oxo-2H-chromene-3-carboxylic acid (3-imidazo[1,2-a]pyridin-2-yl-phenyl)-amideYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIEA (0.030 mL, 0.17 mmol) was added to 8-(4-morpholinylmethyl)-3-carboxy-6-methoxy-coumarin (0.050 g, 0.16 mmol) and HATU (0.065 g, 0.17 mmol) in 1 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 (0.033 g, 0.16 mmol) was added and allowed to react overnight, when a yellow solid precipitated out of solution. The precipitate was filtered and dried under suction and then in vacuo to give 0.047 g of 1541D in a 59% yield: LCMS (ESI) m/z 511 (MH+).

Workup

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

Sources & evidence

ORD record
ord-f283fc0316b440feae461ad363ea6281
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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