Tributylphosphine → HCID 57665153, compound

HRID 1717365Notes

Reaction equation

HRID 1717365 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:16][C:15]=3[OH:25])[C:11]=2[CH2:12]O)=[O:6])[CH2:3][CH2:2]1.C(P(CCCC)CCCC)CCC.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1.C(OCC)(=O)C>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]3[C:14]4[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:16][C:15]=4[O:25][CH2:12][C:11]=23)=[O:6])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 57665023HCID 57665023, compound

Product 1

HCID 57665153HCID 57665153, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Cyclopropyl-1-{4-[(ethylamino)carbonyl]-2-hydroxyphenyl}-5-(hydroxymethyl)-1H-1,2,3-triazole-4-carboxamide (300 mg, 0.868 mmol) obtained in Example 317 was dissolved in THF (6.0 ml), tributylphosphine (0.300 ml, 1.13 mmol, 1.3 eq.) and ADDP (290 mg, 1.13 mmol, 1.3 eq.) were added, and the mixture was stirred at room temperature for 7 hr. The reaction mixture was diluted with ethyl acetate (10 ml), and the precipitate was collected by filtration, washed with ethyl acetate and suspended in water. The insoluble component was collected by filtration, washed with water and methanol and dried to give the title compound as a white powder (228 mg, 0.697 mmol, 80.2%).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with ethyl acetate
  3. filtrationThe insoluble component was collected by filtration
  4. washwashed with water and methanol
  5. customdried

Sources & evidence

ORD record
ord-3042d30c2b6e481bae2860ea0e3f6881
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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