P,P-Diphenylphosphinic azide → HCID 22603175, compound

HRID 2308012Notes

Reaction equation

HRID 2308012 reaction equation
O[CH2:2][CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([O:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[CH3:24])[CH2:4][CH3:5].C1(P([N:39]=[N+:40]=[N-:41])(C2C=CC=CC=2)=O)C=CC=CC=1>C1(C)C=CC=CC=1>[N:39]([CH2:2][CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([O:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[CH3:24])[CH2:4][CH3:5])=[N+:40]=[N-:41]

Participants

4

Reactant 2

HCID 199401P,P-Diphenylphosphinic azideHCID 21912371HCID 21912371, compound

Product 1

HCID 22603175HCID 22603175, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (1-hydroxymethyl-propyl)-[3,6-dimethyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-4-yl]-amine in toluene was added diphenylphosphoryl azide and 1,8-diazbicyclo[3,4,0]undec-7-ene at 0° C. The resulting mixture was stirred at rt for 30 min, then heated 75° C. overnight. The reaction mixture was quenched with water and extracted with methylene chloride. The organic layer was separated, dried, concentrated and purified by silica gel Biotage using 1:1 methylene chloride/hexane to methylene chloride as eluent to give (1-azidomethyl-propyl)-[3,6-dimethyl-2-(2,4,6-trimethyl-phenoxy)-pyrid in-4-yl]-amine as a light yellow oil. The oil was reduced with triphenylphospine to give the title compound. 1H NMR (CDCl3) d 6.86(s, 2H), 6.11(s, 1H), 4.02(d, 1H), 3.40(q, 1H), 2.84(m, 2H), 2.28(s, 3H), 2.13(s, 6H), 2.06(s, 6H), 1.61 (m, 2H), 0.98(t, 3H)ppm

Workup

  1. temperatureheated 75° C. overnight
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with methylene chloride
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated
  7. custompurified by silica gel Biotage

Sources & evidence

ORD record
ord-d8bff29b5d7a429c8366056dee895191
Source dataset
uspto-grants-2004_12
Patent number
US06833378B2

Reaction notes

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