Potassium Iodide → HCID 89590921, compound

HRID 522405Notes

Reaction equation

HRID 522405 reaction equation
FC(F)(F)C(O)=O.[C:8]([C@H:12]1[C:45](=[O:46])[N:44]2[CH2:47][C@@H:41]([CH2:42][C@H:43]2[C:48]([O:50][CH3:51])=[O:49])[O:40][C:24]2=[N:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=3[C:32]([O:33][CH:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)=[C:23]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C@@H:17]2[CH2:52][C@H:16]2[O:15][C:14](=[O:53])[NH:13]1)([CH3:11])([CH3:10])[CH3:9].[I-].[K+].[CH3:56][O:57][CH2:58][CH2:59]Br>CN(C=O)C.C(N(CC)CC)C>[C:8]([C@H:12]1[C:45](=[O:46])[N:44]2[CH2:47][C@@H:41]([CH2:42][C@H:43]2[C:48]([O:50][CH3:51])=[O:49])[O:40][C:24]2=[N:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=3[C:32]([O:33][CH:34]3[CH2:39][CH2:38][N:37]([CH2:59][CH2:58][O:57][CH3:56])[CH2:36][CH2:35]3)=[C:23]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C@@H:17]2[CH2:52][C@H:16]2[O:15][C:14](=[O:53])[NH:13]1)([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 809722-Bromoethyl methyl etherHCID 117599199HCID 117599199, compound

Product 1

HCID 89590921HCID 89590921, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

The amine from Step 2 (70.9 mg) was dissolved in DMF (0.3 mL) and triethylamine (53 μl), potassium iodide (1.6 mg) and 2-bromoethyl methyl ether (20 μl) were added sequentially. The reaction mixture was stirred at 60° C. for 24 hours. The reaction mixture was then cooled to room temperature and quenched with a saturated solution of sodium bicarbonate. The mixture was extracted (3×) with ethyl acetate and the combined organics were dried with sodium sulfate, filtered and concentrated. Purification of the residue by flash chromatography (ISCO, 0 to 10% methanol in DCM) gave the desired product (50.6 mg). LRMS (ES+) m/z 695.5 (M+H)+.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customquenched with a saturated solution of sodium bicarbonate
  3. extractionThe mixture was extracted (3×) with ethyl acetate
  4. dry with materialthe combined organics were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by flash chromatography (ISCO, 0 to 10% methanol in DCM)

Sources & evidence

ORD record
ord-480c30ff86114defa426b5b9f3fd9a65
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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