N-Phenyl diethanolamine → HCID 76684686, compound

HRID 1752787Notes

Reaction equation

HRID 1752787 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([SH:12])[N:11]=[C:4]2[N:3]=1.[C:13]1([N:19]([CH2:23][CH2:24]O)[CH2:20][CH2:21][OH:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([S:12][CH2:24][CH2:23][N:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:20][CH2:21][OH:22])[N:11]=[C:4]2[N:3]=1

Participants

6

Reactant 4

HCID 8416N-Phenyl diethanolamineHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178426287HCID 178426287, compound

Product 1

HCID 76684686HCID 76684686, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-thiol (500 mg, 2.78 mmol), N-phenyldiethanolamine (458 mg, 2.53 mmol), tetrahydrofuran (5 mL) and a magnetic stirring bar were added to a 50 mL RBF. Triphenylphosphine (861 mg, 3.28 mmol) was added followed by the slow addition of diisopropylazodicarboxylate (664 mg, 3.28 mmol) via syringe over 15 minutes. The mixture was stirred at room temperature for 2 h. Progress of the reaction was monitored by HPLC. The reaction was concentrated then ethyl acetate (40 mL) was added which caused a precipitate to form. The precipitate was removed by filtration and rinsed with ethyl acetate (4 mL). The organic layer was concentrated. The title compound was purified by silica gel column chromatography with a gradient elution of 65-100% ethyl acetate in hexanes. Fractions were combined and concentrated under reduced pressure. The resulting solid was triturated with ethyl acetate (3 mL) and dried to afford the title compound as a white solid (274 mg, 32% yield). 1H NMR (DMSO-d6, 400 MHz) δ ppm: 7.16 (m, 3H), 6.90 (d, 2H), 6.59 (t, 1H), 4.71 (t, 1H), 3.73 (m, 2H), 3.56 (q, 2H), 3.46 (t, 2H), 3.35 (m, 2H), 2.74 (s, 3H), 2.56 (s, 3H). EM (calc.): 343.1; MS (ESI) m/e: 344.2 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. additionethyl acetate (40 mL) was added which
  3. customto form
  4. customThe precipitate was removed by filtration
  5. washrinsed with ethyl acetate (4 mL)
  6. concentrationThe organic layer was concentrated
  7. customThe title compound was purified by silica gel column chromatography with a gradient elution of 65-100% ethyl acetate in hexanes
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting solid was triturated with ethyl acetate (3 mL)
  10. customdried

Sources & evidence

ORD record
ord-766ae8a304c042eb9796a2730adb47c8
Source dataset
uspto-grants-2015_10
Patent number
US09163027B2

Reaction notes

Loading…