Sodium Iodide → HCID 178453921, compound

HRID 2061628Notes

Reaction equation

HRID 2061628 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15]Br)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].[S:26]1[C:30]2[CH2:31][C@@H:32]([NH2:35])[CH2:33][CH2:34][C:29]=2[N:28]=[C:27]1[NH2:36]>C(#N)C>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][NH:35][C@H:32]2[CH2:33][CH2:34][C:29]3[N:28]=[C:27]([NH2:36])[S:26][C:30]=3[CH2:31]2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 115211532,6-Diamino-4,5,6,7-tetrahydrobenzothiazole, (S)-HCID 178453878HCID 178453878, compound

Product 1

HCID 178453921HCID 178453921, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Bromide 17 (1.1 g, 3.6 mmol), cesium carbonate (1.47 g, 4.5 mmol), and sodium iodide (0.68 g, 4.5 mmol) were added to a solution of compound 19 (0.63 g, 3.0 mmol) in acetonitrile (40 mL). After refluxing for 48 hours, the mixture was evaporated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, and dried over anhydrous sodium sulfate (Na2SO4). Flash column chromatography (MeOH/EtOAc, 1:6) gave compound 20 as a colorless oil (0.8 g, 61%). 1H NMR (CDCl3, 300 MHz) δ 4.93 (s, 2H), 4.02 (d, J=7.4 Hz, 1H), 3.50-3.30 (m, 1H), 3.10-2.95 (m, 1H), 2.80-2.35 (m, 8H), 2.05-1.90 (m, 3H), 1.85-1.60 (m, 3H), 1.55-1.00 (m, 9H), 1.44 (s, 9H), 0.87 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureAfter refluxing for 48 hours
  2. customthe mixture was evaporated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate (Na2SO4)

Sources & evidence

ORD record
ord-950253ba342b4c82bfad96e9c5d367d0
Source dataset
uspto-grants-2012_10
Patent number
US08283368B2

Reaction notes

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