Isopropylamine → HCID 24853271, compound

HRID 1260352Notes

Reaction equation

HRID 1260352 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 (6 H) 2.22 (3 H) 3.65-3.83 (1 H) 6.99 (1 H) 7.32 (1 H) 7.43 (1 H) 7.61 (1 H); 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-5c41e3c223f74dad9042ab1c5dcecae0
Source dataset
uspto-grants-2013_06
Patent number
US08470813B2

Reaction notes

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