1,1'-Carbonyldiimidazole → 5-((6-Bromobenzo[d]thiazol-2-yl)methyl)-1,3,4-oxadiazol-2-ol

HRID 1754256Notes

Reaction equation

HRID 1754256 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]=[C:7]([CH2:9][C:10]([NH:12][NH2:13])=[O:11])[S:8][C:4]=2[CH:3]=1.C1N=CN([C:21](N2C=NC=C2)=[O:22])C=1>ClCCCl>[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]=[C:7]([CH2:9][C:10]3[O:11][C:21]([OH:22])=[N:13][N:12]=3)[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 899219952-(6-Bromobenzo[d]thiazol-2-yl)acetohydrazide

Product 1

HCID 1785189165-((6-Bromobenzo[d]thiazol-2-yl)methyl)-1,3,4-oxadiazol-2-olYield 54.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of 2-(6-bromobenzo[d]thiazol-2-yl)acetohydrazide (500 mg, 1.75 mmol) (described in WO 2011/074560) in 1,2-dichloroethane (15 mL) at 0° C. was added CDI (340 mg, 2.10 mmol) then the reaction mixture allowed to warm to room temperature and stirred for 2 h. The reaction mixture was concentrated under reduced pressure and the residue purified on silica gel chromatography eluting with 0 to 10% MeOH/DCM to give Compound 51a (296 mg, 54% yield) as a white solid. LCMS=0.84 min using analytical method (M), 502.0 (M+H). 1H NMR (400 MHz, CDCl3 containing CD3OD) δ 8.02 (d, J=1.8 Hz, 1H), 7.84 (d, J=8.5 Hz, 1H), 7.59 (dd, J=8.7, 1.9 Hz, 1H), 4.38 (s, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue purified on silica gel chromatography
  3. washeluting with 0 to 10% MeOH/DCM

Sources & evidence

ORD record
ord-446694e84ab248bfaa84e84371fa069d
Source dataset
uspto-grants-2015_10
Patent number
US09169240B2

Reaction notes

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