Triphenylphosphine → HCID 66977367, compound

HRID 1041908Notes

Reaction equation

HRID 1041908 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[N:5]=[C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1.[N:18]1([CH2:24][CH2:25]O)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.C(OCC)C>[C:14]([C:4]1[CH:3]=[C:2]([NH2:1])[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:25][CH2:24][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:9][CH:8]=2)[N:5]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 595579504-(5-Amino-3-tert-butyl-pyrazol-1-yl)phenol

Product 1

HCID 66977367HCID 66977367, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(5-amino-3-tert-butyl-pyrazol-1-yl)-phenol (WO2005/110994, 0.462 g, 2 mmol), 2-morpholin-4-yl-ethanol (0.327 g, 2.5 mmol) and triphenylphosphine (1.05 g, 4 mmol) in THF (5 mL) under a nitrogen atmosphere was treated with diisopropyl azodicarboxylate (0.808 mg, 4 mmol). The reaction mixture was stirred at RT for 16 H, then diluted with diethyl ether. The organic layer was washed with water. The resulting aqueous layer was basified with potassium carbonate and extracted with EtOAc. The resulting organic layer was washed with aq. citric acid solution, and the resulting aqueous layer was basified with potassium carbonate, and extracted with EtOAc (three times). The resulting organic layer was dried (Na2SO4), evaporated to dryness then sonicated with diethyl ether (10 mL) and filtered to give the title compound (0.297 g, 43%) as a white solid. LCMS (Method 5): Rt 0.41, 2.16 min, m/z 345 [MH+]. 1H NMR (400 MHz, CDCl3): δ 7.46-7.39 (2 H, m), 6.98-6.93 (2 H, m), 5.50 (1 H, s), 4.15-4.08 (2 H, m), 3.75 (4 H, t, J 4.5), 3.63 (2 H, bs), 2.83-2.78 (2 H, m), 2.59 (4 H, t, J 4.3), 1.34-1.26 (9 H, m).

Workup

  1. washThe organic layer was washed with water
  2. extractionextracted with EtOAc
  3. washThe resulting organic layer was washed with aq. citric acid solution
  4. extractionextracted with EtOAc (three times)
  5. dry with materialThe resulting organic layer was dried (Na2SO4)
  6. customevaporated to dryness
  7. customthen sonicated with diethyl ether (10 mL)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-8a60fb1a72574534a36fedb45cddaabc
Source dataset
uspto-grants-2013_10
Patent number
US08557797B2

Reaction notes

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