1,1'-Carbonyldiimidazole → HCID 178518918, compound

HRID 1806128Notes

Reaction equation

HRID 1806128 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]([NH:18][NH2:19])=[O:17])[N:13]=2)=[N:6][CH:7]=1.C1N=CN([C:32](N2C=NC=C2)=[O:33])C=1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]3[O:17][C:32]([OH:33])=[N:19][N:18]=3)[N:13]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 866315133-(2-(5-Bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanehydrazide

Product 1

HCID 178518918HCID 178518918, compoundYield 28.31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanehydrazide (0.150 g, 0.345 mmol) in THF (5 mL) was added TEA (0.04814 mL, 0.3454 mmol) and cooled in an ice bath. To this mixture was added CDI (0.0672 g, 0.414 mmol) in one portion. The mixture was allowed to warm to ambient temperature and was then heated at 50° C. overnight. The reaction was concentrated to dryness, dissolved in CH2Cl2 and washed with water, dried over Na2SO4, concentrated, to a residue that was purified by preparative HPLC to give the title compound (0.045 g, 28.31% yield) was white solids. 1H NMR (d6 DMSO) δ 2.91 (s, 4H), 6.75 (s, 1H), 7.10 (d, J=7.8 Hz, 2H), 7.21 (t, J=7.4 Hz, 1H), 7.40 (d, J=2.1 Hz, 1H), 7.44 (t, J=7.9 Hz, 2H), 8.22 (d, J=2.1 Hz, 1H), 11.03 (br s, 1H), 12.04 (br s, 1H).

Workup

  1. temperaturecooled in an ice bath
  2. temperaturewas then heated at 50° C. overnight
  3. concentrationThe reaction was concentrated to dryness
  4. dissolutiondissolved in CH2Cl2
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated, to a residue that
  8. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-3a85f8feb2054061aa63f4f9ae2926a9
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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