Triphenylphosphine → HCID 76071820, compound

HRID 2275872Notes

Reaction equation

HRID 2275872 reaction equation
[N:1]([CH2:4][C@H:5]([NH:10][C:11]([C:13]1[N:17]2[CH:18]=[CH:19][CH:20]=[C:21]([O:22][CH2:23][C:24]3[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=3[F:31])[C:16]2=[N:15][C:14]=1[CH3:32])=[O:12])[CH2:6][CH2:7][CH2:8][CH3:9])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[NH2:1][CH2:4][C@H:5]([NH:10][C:11]([C:13]1[N:17]2[CH:18]=[CH:19][CH:20]=[C:21]([O:22][CH2:23][C:24]3[C:25]([F:31])=[CH:26][CH:27]=[CH:28][C:29]=3[F:30])[C:16]2=[N:15][C:14]=1[CH3:32])=[O:12])[CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 86717944HCID 86717944, compound

Product 1

HCID 76071820HCID 76071820, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

42 mg of N-[(2R)-1-azidohexan-2-yl]-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]-pyridine-3-carboxamide (Example 44A, 0.095 mmol) were initially charged in 0.78 ml of THF/water (10:1.5), 28.3 mg of triphenylphosphine (0.108 mmol) were added and the mixture was stirred at RT overnight. The reaction mixture was concentrated and the residue was purified by preparative thick-layer chromatography (mobile phase ethyl acetate:dichloromethane:diethylamine=2:1:0.1). The combined product fractions were purified by preparative HPLC (RP18 column, mobile phase: acetonitrile/water gradient with addition of 0.1% TFA). The product-containing fractions were taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution. The organic phase was dried over sodium sulphate, filtered and concentrated. This gave 17 mg of the title compound (41% of theory).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by preparative thick-layer chromatography (mobile phase ethyl acetate:dichloromethane:diethylamine=2:1:0.1)
  3. customThe combined product fractions were purified by preparative HPLC (RP18 column, mobile phase: acetonitrile/water gradient with addition of 0.1% TFA)
  4. washwashed with saturated aqueous sodium bicarbonate solution
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-02002b2d4c864dbfb2f15e83461b0f60
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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