HCID 57590734, compound → HCID 67519890, compound

HRID 1783802Notes

Reaction equation

HRID 1783802 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]3[N:15]([C:16]=2[C:17](=[O:19])[CH3:18])[CH:14]=[CH:13][S:12]3)[CH:6]=[CH:7][CH:8]=1>COC(OC)N(C)C>[CH3:14][N:15]([CH3:16])[CH:11]=[CH:18][C:17]([C:16]1[N:15]2[C:11]([S:12][CH:13]=[CH:14]2)=[N:10][C:9]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:19]

Participants

3

Reactant 1

HCID 57590734HCID 57590734, compound

Product 1

HCID 67519890HCID 67519890, compoundYield 165.7%

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

A 100 ml round bottom flask was charged with the 1-[6-(3-methoxyphenyl)imidazo [2,1-b][1,3]thiazol-5-yl]ethanone (17.95 g, 62 mmol) and dimethylformamide dimethylacetal (120 ml). The mixture was refluxed for 72 hours and then cooled to room temperature. The mixture was concentrated in vacuo and the residue was purified by flash chromatography (ethyl acetate), giving a pale yellow solid (16.82 g). 300 MHz 1H NMR (DMSO-d6) δ: 8.40 (d, J=4.4 Hz, 1H), 7.59 (d, J=12.5 Hz, 1H), 7.41 (d, J=4.4 Hz, 1H), 7.37 (t, J=7.7 Hz, 1H), 7.17-7.21 (m, 2H), 6.99-7.03 (m, 1H), 5.15 (d, J=12.5 Hz, 1H), 3.79 (s, 3H), 3.04 (s, 3H), 2.44 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed for 72 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by flash chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-1335e176c04444f29e6d6404fe72b4b0
Source dataset
uspto-grants-2009_03
Patent number
US07501430B2

Reaction notes

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