Methanesulfonyl chloride → HCID 67266028, compound

HRID 1685758Notes

Reaction equation

HRID 1685758 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]=[C:12]([C:14]3[S:18][C:17]([CH2:19][N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[C:16]([CH3:25])[CH:15]=3)[O:11][N:10]=2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C(Cl)Cl>[CH2:21]([N:20]([CH2:19][C:17]1[S:18][C:14]([C:12]2[O:11][N:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH2:2][NH:1][S:36]([CH3:35])(=[O:38])=[O:37])=[CH:4][CH:5]=3)[N:13]=2)=[CH:15][C:16]=1[CH3:25])[CH2:23][CH3:24])[CH3:22]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67265704HCID 67265704, compound

Product 1

HCID 67266028HCID 67266028, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of {5-[3-(4-aminomethyl-phenyl)-[1,2,4]oxadiazol-5-yl]-3-methyl-thiophen-2-ylmethyl}-diethyl-amine (60 mg, 168 μmol) and DIPEA (33 mg, 252 μmol) in DCM (10 mL), methanesulfonyl chloride (23 mg, 202 μmol) is added. The mixture is stirred at rt for 15 h before it is diluted with DCM and washed with sat. aq. NaHCO3 solution. The washing is extracted back three times with DCM, the organic extracts are combined, dried over MgSO4, filtered and concentrated. The crude product is purified by prep. HPLC. The product containing fractions are combined and concentrated. The product is dissolved in methanol and filtered over Amberlyst A21. The filtrate is evaporated and dried to give the title compound (10 mg) as a colourless resin; LC-MS: tR=0.52 min; [M+1]+=435.03; 1H NMR (CDCl3): δ1.14 (t, J=7.0 Hz, 6H), 2.27 (s, 3H), 2.68 (q, J=6.8 Hz, 4H), 2.93 (s, 3H), 3.79 (s, 2H), 4.42 (d, J=5.8 Hz, 2H), 5.04-5.10 (m, 1H), 7.51 (d, J=8.3 Hz, 2H), 7.68 (s, 1H), 8.15 (d, J=8.3 Hz, 2H).

Workup

  1. washwashed with sat. aq. NaHCO3 solution
  2. extractionThe washing is extracted back three times with DCM
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by prep
  7. additionThe product containing fractions
  8. concentrationconcentrated
  9. dissolutionThe product is dissolved in methanol
  10. filtrationfiltered over Amberlyst A21
  11. customThe filtrate is evaporated
  12. customdried

Sources & evidence

ORD record
ord-7635389c4198491da4bbd69fb4c24ca1
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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