Isopropylamine → HCID 24853271, compound

HRID 2245372Notes

Reaction equation

HRID 2245372 reaction equation
[I-].[F:2][C:3]1([F:27])[O:7][C:6]2[CH:8]=[CH:9][C:10]([N:12]3[CH:16]=[C:15]([CH3:17])[S:14]/[C:13]/3=[N:18]\[C:19]([N:21]3[CH:25]=[CH:24][N+](C)=C3)=[O:20])=[CH:11][C:5]=2[O:4]1.[CH:28](N(C(C)C)CC)(C)C.CC(N)C>C(#N)C>[F:2][C:3]1([F:27])[O:7][C:6]2[CH:8]=[CH:9][C:10]([N:12]3[CH:16]=[C:15]([CH3:17])[S:14]/[C:13]/3=[N:18]\[C:19]([NH:21][CH:25]([CH3:28])[CH3:24])=[O:20])=[CH:11][C:5]=2[O:4]1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 87463844HCID 87463844, compound

Product 1

HCID 24853271HCID 24853271, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

Into a 20 mL vial, a solution of (Z)-1-(3-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-5 -methylthiazol-2(3H)-ylidenecarbamoyl)-3 -methyl-1H-imidazol-3-ium iodide (Example 40B, 48 mg, 0.09 mmol) dissolved in acetonitrile (0.5 mL) was added followed by the addition of diisopropylethylamine (21 μL, 0.12 mmol) dissolved in acetonitrile(0.5 mL). Then, to the solution was added propan-2-amine (5.9 mg, 0.10 mmol) dissolved in acetonitrile (0.5 mL). The vial was capped and shaken overnight at room temperature. The reaction was checked by LC/MS and concentrated to dryness. The residue was dissolved in 1:1 DMSO/MeOH and purified by reverse phase HPLC (acetonitrile/water 0.1% TFA gradient elution method) to supply the titled compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 1.07 (6H) 2.22 (3H) 3.65-3.83 (1H) 6.99 (1H) 7.32 (1H) 7.43 (1H) 7.61 (1H); MS (ESI) m/z 356 (M+H)+

Workup

  1. additionwas added
  2. customThe vial was capped
  3. concentrationconcentrated to dryness
  4. dissolutionThe residue was dissolved in 1:1 DMSO/MeOH
  5. custompurified by reverse phase HPLC (acetonitrile/water 0.1% TFA gradient elution method) to supply the titled compound

Sources & evidence

ORD record
ord-38f6cadbde7d4112ab8357d86ae9be2b
Source dataset
uspto-grants-2010_03
Patent number
US07683084B2

Reaction notes

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