(-)-Epichlorohydrin → HCID 67257360, compound

HRID 509626Notes

Reaction equation

HRID 509626 reaction equation
[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][CH2:12][C:13]3[NH:14][CH:15]=[C:16]([C:18]4[S:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH2:23]([C@@H:25]1[O:27][CH2:26]1)[Cl:24]>ClCCCl>[Cl:24][CH2:23][C@H:25]([OH:27])[CH2:26][N:14]1[CH:15]=[C:16]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[C:13]1[CH2:12][CH2:11][C:9]1[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]2[N:8]=1

Participants

4

Reactant 2

HCID 2734062(-)-EpichlorohydrinHCID 178423941HCID 178423941, compound

Product 1

HCID 67257360HCID 67257360, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-Methyl-2-[2-(4-thiophen-2-yl-1H-imidazol-2-yl)-ethyl]-[1,2,4]triazolo[1,5-a]pyridine (48 mg, 0.16 mmol) in 1,2-dichloroethane (1.5 mL) was added (R)-(−)-epichlorohydrin (80 μL, 1.00 mmol), the reaction vessel was capped and stirred at 100° C. for 16 hours. The volatiles were removed in vacuo and the residue purified by preparative LC-MS to yield the title compound. 6% yield, LC-MS: m/z=402.1 (MH+), tR=0.49 minutes, method B.

Workup

  1. customthe reaction vessel was capped
  2. customThe volatiles were removed in vacuo
  3. customthe residue purified by preparative LC-MS

Sources & evidence

ORD record
ord-6687fc6df47348a18735a3030ed22fc8
Source dataset
uspto-grants-2015_08
Patent number
US09096589B2

Reaction notes

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