Diisopropylethylamine → HCID 86679292, compound

HRID 1519733Notes

Reaction equation

HRID 1519733 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH:34]([C:36]1[CH:41]=[CH:40][C:39](/[CH:42]=[CH:43]/[C:44]#[C:45][C:46]2[CH:54]=[CH:53][C:49]([C:50]([OH:52])=O)=[CH:48][CH:47]=2)=[CH:38][CH:37]=1)=[O:35].Cl.[CH3:56][NH:57][C:58](=[O:66])[C@H:59]([C:62](=[O:65])[O:63][CH3:64])[NH:60][CH3:61]>O.C(OCC)(=O)C.CN(C=O)C>[CH:34]([C:36]1[CH:37]=[CH:38][C:39](/[CH:42]=[CH:43]/[C:44]#[C:45][C:46]2[CH:47]=[CH:48][C:49]([C:50](=[O:52])[N:60]([CH:59]([C:58]([NH:57][CH3:56])=[O:66])[C:62]([O:63][CH3:64])=[O:65])[CH3:61])=[CH:53][CH:54]=2)=[CH:40][CH:41]=1)=[O:35]

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)2×HCID 86679246N,N2,O-trimethyl-3-oxoserinamide hydrochloride2×HCID 86679291HCID 86679291, compound

Product 1

HCID 86679292HCID 86679292, compoundYield 74.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HATU (1.1 g) and DIPEA (1.0 mL) were added to a DMF (5.0 mL) solution of 4-[(E)-4-(4-formylphenyl)but-3-en-1-yn-1-yl)benzoic acid (0.54 g) as obtained in Example 23-(2), and the mixture was stirred for 2 hours and 20 minutes at room temperature. HATU (1.1 g) was further added, and the mixture was stirred for 40 minutes at room temperature. N,N2,O-trimethyl-3-oxoserinamide hydrochloride (Intermediate 5-2, 0.57 g) was added, and the mixture was stirred for 20 minutes at 80° C. The reaction mixture was cooled to room temperature, and ethyl acetate and water were added to isolate the organic layer. The extract was washed sequentially with water and brine, and dried over anhydrous magnesium sulfate. The desiccant was filtered out, and then the solvent was distilled off under reduced pressure. Chloroform, IPE and ethyl acetate were added to the resulting residue, the insolubles were filtered out, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by OH type silica gel column chromatography (gradient elution with chloroform/methanol=100/0→10/1) to obtain 1-formyl-4-[(1E)-4-(4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}phenyl)but-1-en-3-yn-1-yl]benzene (orange oil) (0.61 g, 74%).

Workup

  1. customas obtained in Example 23-(2)
  2. stirringthe mixture was stirred for 40 minutes at room temperature
  3. stirringthe mixture was stirred for 20 minutes at 80° C
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customto isolate the organic layer
  6. washThe extract was washed sequentially with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe desiccant was filtered out
  9. distillationthe solvent was distilled off under reduced pressure
  10. additionChloroform, IPE and ethyl acetate were added to the resulting residue
  11. filtrationthe insolubles were filtered out
  12. concentrationthe filtrate was concentrated under reduced pressure
  13. customThe resulting residue was purified by OH type silica gel column chromatography (gradient elution with chloroform/methanol=100/0→10/1)

Sources & evidence

ORD record
ord-d55d9f9408f84526bf49df45453ed99c
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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