Methanesulfonyl chloride → HCID 25255271, compound

HRID 219947Notes

Reaction equation

HRID 219947 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([F:26])[CH:17]=3)[N:12]=2)[CH:5]=[CH:6][C:7]=1[N:8]([CH3:10])[CH3:9].[S:27](Cl)([CH3:30])(=[O:29])=[O:28]>N1C=CC=CC=1>[CH3:10][N:8]([CH3:9])[C:7]1[CH:6]=[CH:5][C:4]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([F:26])[CH:17]=3)[N:12]=2)=[CH:3][C:2]=1[NH:1][S:27]([CH3:30])(=[O:29])=[O:28]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 67528662HCID 67528662, compound

Product 1

HCID 25255271HCID 25255271, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl 4-{5-[3-amino-4-(dimethylamino)phenyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate was taken up in Pyridine (750 μL) and mesylchloride (40 μL; 0.46 mmol) was added and stirred at RT for 72 h. After the time, the reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (DCM:MeOH from 100:0 to 90:10) to give the title compound as a yellow powder (150 mg; 88%, 2 steps). 1H NMR (DMSO-d6, 300 MHz) δ 9.07 (bs, 1H), 8.13-8.08 (m, 1H), 8.04-7.91 (m, 4H), 7.23 (d, J=8.7 Hz, 1H), 3.90 (s, 3H), 3.14 (s, 3H), 2.88 (s, 6H). LC/MS (Method B): 435.3 (M+H)+. HPLC (Method A) Rt. 4.33 min (purity: 94.4%).

Workup

  1. concentrationAfter the time, the reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography (DCM:MeOH from 100:0 to 90:10)

Sources & evidence

ORD record
ord-7a1a5e3e85b24831a5aec46547889f92
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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