Iodoethane → HCID 178466033, compound

HRID 1422966Notes

Reaction equation

HRID 1422966 reaction equation
[CH2:1](I)[CH3:2].[OH:4][C:5]1[CH:6]=[C:7]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]1[O:12][CH2:11][CH:10]([C@H:19]3[CH2:24][CH2:23][C@H:22]([NH:25][C:26]([C:28]4[CH:29]=[CH:30][C:31]5[S:36][CH2:35][C:34](=[O:37])[NH:33][C:32]=5[CH:38]=4)=[O:27])[CH2:21][CH2:20]3)[CH2:9][C:8]2=1.[H-].[Na+]>CN(C)C=O>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]1[O:12][CH2:11][CH:10]([C@H:19]3[CH2:24][CH2:23][C@H:22]([NH:25][C:26]([C:28]4[CH:29]=[CH:30][C:31]5[S:36][CH2:35][C:34](=[O:37])[NH:33][C:32]=5[CH:38]=4)=[O:27])[CH2:21][CH2:20]3)[CH2:9][C:8]2=1)[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydride2×HCID 178516917HCID 178516917, compound

Product 1

HCID 178466033HCID 178466033, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl iodide (6 μL, 0.07 mmol, 1.0 eq) is added at room temperature to a stirred solution of 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid [trans-4-(6-hydroxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-yl)-cyclohexyl]-amide (40 mg, 0.07 mmol, 1.0 eq) in N,N-dimethylformamide (4 mL), followed by sodium hydride (55% purity, 3.2 mg, 0.07 mmol, 1.0 eq). After 2 hours stirring at room temperature, 1.0 additional equivalent of ethyl idodide and sodium hydride are added to the reaction mixture that is stirred at room temperature for one hour. Then solvent is evaporated and the crude is extracted with dichloromethane (3×10 mL) and water (10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by preparative HPLC to afford 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid [trans-4-(6-ethoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-yl)-cyclohexyl]-amide as an off-white lyophilizated powder (11 mg, 27% yield).

Workup

  1. stirringis stirred at room temperature for one hour
  2. customThen solvent is evaporated
  3. extractionthe crude is extracted with dichloromethane (3×10 mL) and water (10 mL)
  4. dry with materialThe combined organic layers are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue that
  8. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-6ca67eb5ae4044dabc1321072efe81a9
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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