Diisopropylethylamine → HCID 58504166, compound

HRID 2407668Notes

Reaction equation

HRID 2407668 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:7]=1.FC(F)(F)C(O)=O.[Cl:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([NH:28][CH2:29][CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[O:27])=[CH:24][C:23]=1[O:38][CH3:39].C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[Cl:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([NH:28][CH2:29][CH:30]2[CH2:31][CH2:32][N:33]([CH2:2][C:3]3[O:4][C:5]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)=[N:6][N:7]=3)[CH2:34][CH2:35]2)=[O:27])=[CH:24][C:23]=1[O:38][CH3:39]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 3149412-(Chloromethyl)-5-phenyl-1,3,4-oxadiazoleHCID 66989233HCID 66989233, compound

Product 1

HCID 58504166HCID 58504166, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

2-(Chloromethyl)-5-phenyl-1,3,4-oxadiazole (31 mg, prepared according to the reported preparation in Natero, R.; et al. Synth. Commun. 2004, 34, 2523) was added to a solution of the compound prepared in Example 11 (60 mg) and diisopropylethylamine (0.083 mL) in N,N-dimethylformamide (0.8 mL). The solution was heated to 100° C. overnight. The reaction was cooled to room temperature, diluted with ethyl acetate and washed twice with a saturated aqueous sodium bicarbonate solution. The organic phase was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1, then ethyl acetate) to obtain the title compound (36 mg) having the following physical data.

Workup

  1. customaccording to the reported preparation in Natero, R
  2. temperatureThe reaction was cooled to room temperature
  3. washwashed twice with a saturated aqueous sodium bicarbonate solution
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-c756b914f445429eb093d42db261b960
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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