Iodine → HCID 68183030, compound

HRID 1615568Notes

Reaction equation

HRID 1615568 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]2[C:12]3[N:21]=[C:20]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[S:19][C:13]=3[C:14](=[O:18])[NH:15][CH2:16][CH:17]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].C(=O)(O)[O-].[Na+].[I-:33].[K+].II>C(#N)C.O.CC(=O)OCC.S([O-])([O-])(=O)=S.[Na+].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3([O:8][C:7](=[O:9])[C:6]=2[CH:10]=1)[CH:17]([I:33])[CH2:16][NH:15][C:14](=[O:18])[C:13]1[S:19][C:20]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[N:21][C:12]3=1

Participants

9

Reactant 4

HCID 807IodineHCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 68182986HCID 68182986, compound

Product 1

HCID 68183030HCID 68183030, compoundYield 82.6%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

5-chloro-2-[2-(morpholin-4-yl)-4-oxo-5,6-dihydro-4H-[1,3]thiazolo[5,4-c]azepin-8-yl]benzoic acid (0.0500 g, 0.123 mmol) was dissolved in acetonitrile (0.50 mL) and saturated aqueous sodium bicarbonate solution (2.5 mL), then added a solution of potassium iodide (0.102 g, 0.616 mmol) and iodine (0.0406 g, 0.160 mmol) in water (1.0 mL) dropwise and the solution was stirred at room temperature for 16 hours. The reaction mixture was diluted with EA and 15% aqueous sodium thiosulfate solution and the mixture was stirred for 20 minutes. The layers were separated and the aqueous layer was extracted twice more with EA. The combined organic layer was then washed with water and brine then dried over anhydrous sodium sulfate and concentrated. The residue was purified using column chromatography on silica gel (12 gr Analogix column, gradient DCM to 60% EA in DCM over 15 minutes) to give the product (0.0540 g, 82%). LCMS: (AA) ES+ 532, 534. 1H NMR (400 MHz, d6-DMSO) δ: 8.44 (t, J=4.8 Hz, 1H), 8.07-7.90 (m, 1H), 7.92-7.72 (m, 2H), 5.12-4.91 (m, 1H), 3.93-3.81 (m, 1H), 3.77-3.65 (m, 1H), 3.61-3.48 (m, 4H), 3.23-3.08 (m, 4H).

Workup

  1. stirringthe mixture was stirred for 20 minutes
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice more with EA
  4. washThe combined organic layer was then washed with water and brine
  5. dry with materialthen dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified
  8. customon silica gel (12 gr Analogix column, gradient DCM to 60% EA in DCM over 15 minutes)

Sources & evidence

ORD record
ord-2e04fa339a894fbbaef1d8d3fe7f8d1d
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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