Propargyl bromide → HCID 21913055, compound

HRID 1352647Notes

Reaction equation

HRID 1352647 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][CH2:20][OH:21])[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]3[N:15]=[N:16][N:17]=[C:9]3[C:8]=2[N:18]=1)[CH3:2].OCCNC(=O)OC(C)(C)C.Br[CH2:34][C:35]#[C:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(Br)C#C>>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][CH2:20][O:21][CH2:34][C:35]#[C:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]3[N:15]=[N:16][N:17]=[C:9]3[C:8]=2[N:18]=1)[CH3:2]

Participants

5

Reactant 4

HCID 7842Propargyl bromideHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 10987157(3-Bromoprop-1-yn-1-yl)benzeneHCID 21913508HCID 21913508, compound

Product 1

HCID 21913055HCID 21913055, compound

Procedure

The general method described in Part A of Example 81 was followed, using 2-(8-ethoxymethyl-5,6-dimethyl-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridin-7-yl)ethanol (4.51 g, 15.5 mmol) in lieu of tert-butyl 2-hydroxyethylcarbamate and 3-bromo-1-phenylpropyne, prepared as described in Part A of Example 7, in lieu of propargyl bromide. The crude product was triturated with diethyl ether, isolated by filtration, and dried under reduced pressure to provide 5.93 g of 8-ethoxymethyl-5,6-dimethyl-7-{2-[(3-phenylprop-2-ynyl)oxy]ethyl}-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridine as a yellow solid.

Workup

  1. customprepared
  2. customThe crude product was triturated with diethyl ether
  3. customisolated by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-93b502fbd11d4eb5ab54d39ac1e5800f
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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