Methanesulfonyl chloride → HCID 178505112, compound

HRID 1845746Notes

Reaction equation

HRID 1845746 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2C(=O)[O:12][N:11]=[C:10]2[C:15]2[C:19]([CH2:20][NH:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[N:18][O:17][N:16]=2)[CH:5]=[CH:6][C:7]=1[F:8].CCN(C(C)C)C(C)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C(#N)C.CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:15]2[C:19]([CH2:20][N:21]([S:40]([CH3:39])(=[O:42])=[O:41])[CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[N:18][O:17][N:16]=2)=[N:11][OH:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58941938HCID 58941938, compound

Product 1

HCID 178505112HCID 178505112, compoundYield 6.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

4-(3-Chloro-4-fluorophenyl)-3-(4-[(2-morpholin-4-ylethyl)amino]methyl-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazol-5(4H)-one (20 mg, 0.047 mmol) was dissolved in anhydrous ACN (200 μL) followed by addition of DIPEA (40 μL, 0.2 mmol) and methanesulfonyl chloride (4.0 μL, 0.052 mmol). The reaction was stirred at 40° C. for 2 hrs. The reactions was then diluted with MeOH and purified by HPLC. The purified fractions were concentrated to dryness, redissolved in EtOH (1 mL) and 2 M of sodium hydroxide in water (0.26 mL) was added. The reaction was stirred at rt for 2 hrs, quenched with acetic acid, diluted with MeOH and purified by preparative LCMS to afford the desired product (1.4 mg). MF=C17H22ClFN6O5S; LCMS calculated for C17H23ClFN6O5S(M+H)+: m/z=477.1.

Workup

  1. custompurified by HPLC
  2. concentrationThe purified fractions were concentrated to dryness
  3. dissolutionredissolved in EtOH (1 mL)
  4. addition2 M of sodium hydroxide in water (0.26 mL) was added
  5. stirringThe reaction was stirred at rt for 2 hrs
  6. customquenched with acetic acid
  7. additiondiluted with MeOH
  8. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-12443dd98300441099c73949cba6b3a3
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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