Diisopropylethylamine → tert-Butyl(2-oxo-2-{[4-(4-pyridinyl)phenyl]amino}ethyl)phenylcarbamate

HRID 1510217Notes

Reaction equation

HRID 1510217 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[C:14]([O:18][C:19]([N:21]([CH2:28][C:29](O)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.CN(C(=[N+](C)C)ON1C2=NC=CC=C2N=N1)C>CN(C)C=O.O>[O:30]=[C:29]([NH:13][C:10]1[CH:11]=[CH:12][C:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:8][CH:9]=1)[CH2:28][N:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:19](=[O:20])[O:18][C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 15126544-(Pyridin-4-yl)anilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21905636N-(tert-Butoxycarbonyl)-N-phenylglycine

Product 1

HCID 69078964tert-Butyl(2-oxo-2-{[4-(4-pyridinyl)phenyl]amino}ethyl)phenylcarbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

[4-(4-Pyridinyl)phenyl]amine (5.35 g) and [(tert-butoxycarbonyl)(phenyl)amino]acetic acid (7.90 g) were dissolved in N,N-dimethylformamide (250 mL), then N,N-diisopropylethylamine (12.0 mL) and N-[(dimethylamino) (3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methylmethanaminium hexafluorophosphate (13.1 g) were added to the mixture at ambient temperature. After stirring at ambient temperature overnight, water (250 mL) was added to the resulting mixture and the mixture was extracted with ethyl acetate (500 mL). The organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by silica gel column chromatography (250 g, n-hexane/ethyl acetate (1:1) then 2% methanol in chloroform). The combined fraction was concentrated in vacuo. The residue was crystallized from 5% ethyl acetate in n-hexane (100 mL). The crystals were collected by filtration and washed with 5% ethyl acetate in n-hexane (20 mL) to afford tert-butyl (2-oxo-2-{[4-(4-pyridinyl)phenyl]amino}ethyl)phenylcarbamate.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (500 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (250 g, n-hexane/ethyl acetate (1:1)
  6. concentrationThe combined fraction was concentrated in vacuo
  7. customThe residue was crystallized from 5% ethyl acetate in n-hexane (100 mL)
  8. filtrationThe crystals were collected by filtration
  9. washwashed with 5% ethyl acetate in n-hexane (20 mL)

Sources & evidence

ORD record
ord-60ca36aea9dc486382792b1bf67aff52
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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