HCID 67529941, compound → HCID 178431878, compound

HRID 602581Notes

Reaction equation

HRID 602581 reaction equation
[I-:1].[NH2:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[N+:10]1[C:14]([CH3:15])=[CH:13][S:12][C:11]=1SC>CO>[I-:1].[F:9][C:7]1[CH:6]=[CH:5][C:4]2[N:10]3[C:14]([CH3:15])=[CH:13][S:12][C:11]3=[NH+:2][C:3]=2[CH:8]=1

Participants

3

Reactant 1

HCID 67529941HCID 67529941, compound

Product 1

HCID 178431878HCID 178431878, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2 g (5.23 mmol) of 3-(2-amino-4-fluorophenyl)-4-methyl-2-(methylsulfanyl)-1,3-thiazol-3-ium iodide obtained in stage B1 were solubilised in MeOH (200 mL) and the solution refluxed for 12 h. Then MeOH was evaporated to yield 7-fluoro-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide (4b) (pale yellow powder, 1.74 g, 99%). Mp=240° C.; 1H NMR (300 MHz, CD3OD) δ=2.83 (3H, d, 0.1=1.3, CH3), 7.03 (1H, q, J=1.3, H5), 7.20-7.27 (1H, m, Ar), 7.47-7.51 (1H, m, Ar), 8.06-8.11 (1H, m, Ar); 13C NMR (75 MHz, CD3OD) δ=14.1, 103.5 (d, J=27), 109.9, 112.1 (d, J=27), 114.0 (d, J=10), 126.9, 133.3, 143.6 (d, J=10), 158.3, 162.0 (d, J=242); HRMS m/z C10H8N2FS [M−I]+ calcd: 207.0387, found: 207.0388. Stage C: Preparation of 7-fluoro-3,9-dimethyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide

Workup

  1. temperaturethe solution refluxed for 12 h
  2. customThen MeOH was evaporated

Sources & evidence

ORD record
ord-015e6a90533941d6a537f5a3e97e53be
Source dataset
uspto-grants-2011_03
Patent number
US07906541B2

Reaction notes

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