Benzyl azide → HCID 68665329, compound

HRID 1893454Notes

Reaction equation

HRID 1893454 reaction equation
[N:1](CC1C=CC=CC=1)=[N+:2]=[N-:3].[C:11]([C:13]1[N:17]2[C:18]3[C:23]([N:24]=[C:25]([NH:26][CH2:27][CH2:28][CH2:29][OH:30])[C:16]2=[N:15][CH:14]=1)=[CH:22][C:21]([C:31]([F:34])([F:33])[F:32])=[CH:20][CH:19]=3)#[CH:12].O=[C:36]1O[C@H:41]([C@H:43]([CH2:45]O)O)[C:39]([O-])=[C:37]1O.[Na+]>C(O)(C)(C)C.O.S([O-])([O-])(=O)=O.[Cu+2]>[C:36]1([N:1]2[CH:12]=[C:11]([C:13]3[N:17]4[C:18]5[C:23]([N:24]=[C:25]([NH:26][CH2:27][CH2:28][CH2:29][OH:30])[C:16]4=[N:15][CH:14]=3)=[CH:22][C:21]([C:31]([F:32])([F:33])[F:34])=[CH:20][CH:19]=5)[N:3]=[N:2]2)[CH:45]=[CH:43][CH:41]=[CH:39][CH:37]=1

Participants

7

Reactant 3

HCID 12152Benzyl azideHCID 23667548Sodium AscorbateHCID 59333283HCID 59333283, compound

Product 1

HCID 68665329HCID 68665329, compoundYield 7%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

To a solution of (azidomethyl)benzene (16 mg, 0.12 mmol) in t-butyl alcohol (0.12 mL) and water (0.12 mL), under argon, was added 3-{[1-ethynyl-7-(trifluoromethyl)imidazo[1,2-a]quinoxalin-4-yl]amino}propan-1-ol as prepared in example 30 (40 mg, 0.12 mmol), copper sulfate (0.2 mg, 0.0012 mmol) and a freshly prepared 1M aqueous solution of sodium ascorbate (0.012 mL, 0.012 mmol). After 18 h at room temperature, a white precipitate was formed. Water was added to the reaction mixture then cooled with an ice bath. The precipitate was filtered, washed with cold water and then dried under vacuum. The crude product was purified by preparative TLC (silica gel, ethyl acetate) to afford the title compound (4 mg, 7%) as a white solid.

Workup

  1. customa white precipitate was formed
  2. temperaturethen cooled with an ice bath
  3. filtrationThe precipitate was filtered
  4. washwashed with cold water
  5. customdried under vacuum
  6. customThe crude product was purified by preparative TLC (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-c82bac3fd4bf42308a56ae5ae1b46f58
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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