Methanesulfonyl chloride → HCID 68578674, compound

HRID 2047328Notes

Reaction equation

HRID 2047328 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH:18]=3)[O:14][N:13]=2)=[CH:7][C:6]=1[CH2:29][CH3:30].CCN(C(C)C)C(C)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl.CC(=O)OCC>[CH2:27]([N:24]([CH2:25][CH3:26])[C:19]1[CH:18]=[C:17]([C:15]2[O:14][N:13]=[C:12]([C:8]3[CH:9]=[C:10]([CH3:11])[C:5]([O:4][CH2:3][CH2:2][NH:1][S:41]([CH3:40])(=[O:43])=[O:42])=[C:6]([CH2:29][CH3:30])[CH:7]=3)[N:16]=2)[CH:22]=[C:21]([CH3:23])[N:20]=1)[CH3:28]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68578282HCID 68578282, compound

Product 1

HCID 68578674HCID 68578674, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of crude (4-{3-[4-(2-amino-ethoxy)-3-ethyl-5-methyl-phenyl]-[1,2,4]oxadiazol-5-yl}-6-methyl-pyridin-2-yl)-diethyl-amine (70 mg, 0.17 mmol) and DIPEA (44 mg, 0.342 mmol) in DCM (2 mL), methane sulfonyl chloride (23 mg, 0.205 mmol) is added. The mixture is stirred at rt for 30 min before it is diluted with EA and washed with sat. aq. NaHCO3-solution. The washing is extracted back three times with EA. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified on prep. TLC plates using heptane:EA 1:1 to give the title compound (34 mg) as a pale yellow oil; LC-MS*: tR=1.12 min; [M+1]+=488.05; 1H NMR (CDCl3): δ 1.25 (t, J=6.8 Hz, 6H), 1.33 (t, J=7.5 Hz, 3H), 2.40 (s, 3H), 2.50 (s, 3H), 2.76 (q, J=7.5 Hz, 2H), 3.09 (s, 3H), 3.57-3.67 (m, 6H), 3.99 (t, J=4.8 Hz, 2H), 4.91 (t, J=5.5 Hz, 1H), 7.01 (s, 1H), 7.10 (s, 1H), 7.88 (s, 1H), 7.89 (s, 1H).

Workup

  1. washwashed with sat. aq. NaHCO3-solution
  2. extractionThe washing is extracted back three times with EA
  3. dry with materialextracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified on prep

Sources & evidence

ORD record
ord-02f25ad5d0ae40f9ba0208e3c77a28c7
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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