Methanesulfonyl chloride → HCID 86646455, compound

HRID 1685762Notes

Reaction equation

HRID 1685762 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[S:11][C:10]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][OH:25])=[CH:19][CH:18]=3)[N:13]=2)=[CH:9][C:8]=1[CH3:26])[CH2:4][CH3:5])[CH3:2].CCN(C(C)C)C(C)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C1COCC1.C(Cl)Cl>[CH2:1]([N:3]([CH2:6][C:7]1[S:11][C:10]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][O:25][S:37]([CH3:36])(=[O:39])=[O:38])=[CH:21][CH:22]=3)[N:13]=2)=[CH:9][C:8]=1[CH3:26])[CH2:4][CH3:5])[CH3:2]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 672654152-{4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethanol

Product 1

HCID 86646455HCID 86646455, compoundYield 134.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 2-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethanol (196 mg, 488 μmol) and DIPEA (84 mg, 732 μmol) in THF (5 mL), methanesulfonyl chloride (126 mg, 976 μmol) is added as a solution in THF (2.5 mL). The reaction mixture is stirred at 0° C. for 1 h, then at rt for 1 h. The mixture is diluted with DCM (100 mL) and washed with brine (3×50 mL). The organic extract is dried over MgSO4, filtered, concentrated and dried to give crude methanesulfonic acid 2-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethyl ester (295 mg); LC-MS: tR=0.59 min; [M+1]+=449.71. b) A solution of methanesulfonic acid 2-{4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethyl ester (295 mg, 658 μmol) in 7 N NH3 in methanol (10 mL) is stirred in a sealed vessel at 80° C. for 16 h. The reaction mixture is concentrated and dried to give the title compound (255 mg) as a pale yellow oil; LC-MS: tR=0.64 min; [M+1]+=370.97.

Workup

  1. waitat rt for 1 h
  2. washwashed with brine (3×50 mL)
  3. extractionThe organic extract
  4. dry with materialis dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried

Sources & evidence

ORD record
ord-8d05328e7ac44ddeb319613fbb94e575
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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