Iodoethane → HCID 66829252, compound

HRID 1685751Notes

Reaction equation

HRID 1685751 reaction equation
[OH:1][CH2:2][C:3]([NH:5][CH2:6][C@H:7]([OH:34])[CH2:8][O:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]2[N:21]=[C:20]([C:22]3[S:23][C:24]([CH2:28][NH:29][CH:30]([CH3:32])[CH3:31])=[C:25]([CH3:27])[CH:26]=3)[O:19][N:18]=2)=[CH:12][C:11]=1[CH3:33])=[O:4].[CH2:35](I)[CH3:36].CCN(C(C)C)C(C)C>CN(C=O)C.N>[NH3:5].[CH2:35]([N:29]([CH2:28][C:24]1[S:23][C:22]([C:20]2[O:19][N:18]=[C:17]([C:13]3[CH:14]=[C:15]([CH3:16])[C:10]([O:9][CH2:8][C@@H:7]([OH:34])[CH2:6][NH:5][C:3](=[O:4])[CH2:2][OH:1])=[C:11]([CH3:33])[CH:12]=3)[N:21]=2)=[CH:26][C:25]=1[CH3:27])[CH:30]([CH3:31])[CH3:32])[CH3:36]

Participants

7

Reactant 3

HCID 6340Iodoethane2×HCID 81531Diisopropylethylamine2×HCID 67265558HCID 67265558, compound

Product 2

HCID 222AmmoniaHCID 66829252HCID 66829252, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-hydroxy-N-[(2S)-2-hydroxy-3-(4-{5-[5-(isopropylamino-methyl)-4-methyl-thiophen-2-yl]-[1,2,4]oxadiazol-3-yl}-2,6-dimethyl-phenoxy)-propyl]-acetamide (284 mg, 0.448 mmol, Example 91), ethyl iodide (423 mg, 2.69 mmol) and DIPEA (354 mg, 2.69 mmol) in DMF (3 mL) is stirred at rt for 1 h, then at 40° C. for 17 h before another portion of DIPEA (54 mg, 0.421 mmol) and ethyl iodide (304 mg, 1.95 mmol) is added. Stirring is continued at 40° C. for 20 h. The mixture is diluted with aq. sat. NH3 (1 mL) and separated by prep. HPLC (Waters XBridge Prep C18, 75×30 mm ID, 10 μm, gradient of acetonitrile in water containing 0.5% of sat. aq. NH3) to give the title compound (94 mg) as a colourless resin; LC-MS*: tR=1.08 min; [M+1]+=517.32.

Workup

  1. customseparated by prep

Sources & evidence

ORD record
ord-d5968ab7d0244c5094b397b65cfb3872
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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