Tributylphosphine → HCID 57665171, compound

HRID 1717379Notes

Reaction equation

HRID 1717379 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([NH:24][CH2:25][CH3:26])=[O:23])=[CH:18][C:17]=3[OH:27])[C:11]=2[CH2:12][CH2:13][CH2:14]O)=[O:6])[CH2:3][CH2:2]1.C(P(CCCC)CCCC)CCC.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]3[C:16]4[CH:21]=[CH:20][C:19]([C:22]([NH:24][CH2:25][CH3:26])=[O:23])=[CH:18][C:17]=4[O:27][CH2:14][CH2:13][CH2:12][C:11]=23)=[O:6])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 68518208HCID 68518208, compound

Product 1

HCID 57665171HCID 57665171, compoundYield 12.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Cyclopropyl-1-{4-[(ethylamino)carbonyl]-2-hydroxyphenyl}-5-(3-hydroxypropyl)-1H-1,2,3-triazole-4-carboxamide (260 mg) obtained in Example 335c) and tributylphosphine (4.1 ml) were dissolved in THF (50 ml), ADDP (4.16 g) was added under an argon atmosphere, and the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure, and the obtained residue was dissolved in ethyl acetate. This ethyl acetate solution was washed with 1N hydrochloric acid, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column (ethyl acetate to ethyl acetate/methanol=5/1) and further triturated with ether to give the title compound as a white powder (30 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in ethyl acetate
  3. washThis ethyl acetate solution was washed with 1N hydrochloric acid
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column (ethyl acetate to ethyl acetate/methanol=5/1)
  7. customfurther triturated with ether

Sources & evidence

ORD record
ord-8cd48f7834074453a16d79e9a198acb1
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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