Diisopropylethylamine → HCID 58158466, compound

HRID 2095918Notes

Reaction equation

HRID 2095918 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([OH:18])=O)[C:11]1=[O:19])[CH3:3].[NH2:20][C:21]1[CH:42]=[CH:41][C:24]([O:25][C:26]2[CH:27]=[CH:28][C:29]3[N:30]([CH:32]=[C:33]([NH:35][C:36]([CH:38]4[CH2:40][CH2:39]4)=[O:37])[N:34]=3)[CH:31]=2)=[C:23]([F:43])[CH:22]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C.O1CCCC1>[CH:38]1([C:36]([NH:35][C:33]2[N:34]=[C:29]3[CH:28]=[CH:27][C:26]([O:25][C:24]4[CH:41]=[CH:42][C:21]([NH:20][C:16]([C:12]5[C:11](=[O:19])[N:10]([C:5]6[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=6[CH:2]([CH3:1])[CH3:3])[CH:15]=[CH:14][CH:13]=5)=[O:18])=[CH:22][C:23]=4[F:43])=[CH:31][N:30]3[CH:32]=2)=[O:37])[CH2:39][CH2:40]1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58158605N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamideHCID 66968863HCID 66968863, compound

Product 1

HCID 58158466HCID 58158466, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[2-(1-Methylethyl)phenyl]-2-oxo-1,2-dihydropyridine-3-carboxylic acid (100 mg, 0.39 mmol), N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (120 mg, 0.35 mmol) and HATU (170 mg, 0.45 mmol) were suspended in N,N-dimethylformamide (3.0 mL), and N,N-diisopropylethylamine (0.12 mL, 0.71 mmol) was added. After stirring at room temperature overnight, the mixture was diluted with ethyl acetate (5.0 mL) and tetrahydrofuran (5.0 mL). The mixture was washed twice with saturated aqueous sodium hydrogen carbonate solution, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=65/35→85/15). The fractions containing the object product were mixed. The solvent was evaporated under reduced pressure, and a small amount of hexane/ethyl acetate (=2/1) was added. The resulting precipitate was collected by filtration to give the title compound (53 mg, 27%) as a white solid.

Workup

  1. washThe mixture was washed twice with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=65/35→85/15)
  5. additionThe fractions containing the object product
  6. additionwere mixed
  7. customThe solvent was evaporated under reduced pressure
  8. additiona small amount of hexane/ethyl acetate (=2/1) was added
  9. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-cd99fc3c465648b9b1f2549a231e911e
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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