Isopropyl iodide → HCID 178493634, compound

HRID 1944751Notes

Reaction equation

HRID 1944751 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([O:30][CH3:31])[CH:24]=3)(=[O:22])=[O:21])[CH2:15][CH2:14]2)=[O:12])[CH3:9])=[CH:4][CH:3]=1.I[CH:33]([CH3:35])[CH3:34].C([O-])([O-])=O.[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH:33]([CH3:35])[CH3:34])=[C:25]([O:30][CH3:31])[CH:24]=3)(=[O:22])=[O:21])[CH2:15][CH2:14]2)=[O:12])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 178493632HCID 178493632, compound

Product 1

HCID 178493634HCID 178493634, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Trans-N—((R)-1-(4-Fluorophenyl)ethyl)-4-(4-hydroxy-3-methoxyphenylsulfonamido)cyclohexanecarboxamide (Example 2, 14 mg, 0.031 mmol), 2-iodopropane (4 ul, 0.037 mmol), K2CO3 (21 mg, 0.155 mmol) and tetrabutylammonium iodide (TBAI, 3 mg, cat) were dissolved in DMF (0.5 ml) and the reaction was stirred at room temperature for 15 hr under nitrogen. LCMS indicated that the reaction was complete, and the crude material was purified via reverse phase chromatography on prep-HPLC (150 mm, C8 luna, 15-20 min run, 10%-100% MeCN in water containing 0.1% TFA). Fractions containing the product were lyophilized to yield the title compound as a white solid (6.4 mg, 42%). MS MH+ 493.1

Workup

  1. customthe crude material was purified via reverse phase chromatography on prep-HPLC (150 mm, C8 luna, 15-20 min run, 10%-100% MeCN in water containing 0.1% TFA)
  2. additionFractions containing the product

Sources & evidence

ORD record
ord-8d1a44a320e04c6fa47a1e6a34d8417f
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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