Methanesulfonyl chloride → HCID 11313549, compound

HRID 495141Notes

Reaction equation

HRID 495141 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:18]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=2[O:16][C:15](=[O:24])[CH:14]=1.CCN(C(C)C)C(C)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]2[O:16][C:15](=[O:24])[CH:14]=[C:13]([O:12][CH2:11][CH2:10][CH2:9][NH:8][S:35]([CH3:34])(=[O:37])=[O:36])[C:18]=2[CH:19]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 11372063HCID 11372063, compound

Product 1

HCID 11313549HCID 11313549, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-Aminopropoxy)-6-chloro-1-benzopyran-2-one trifluoroacetate salt (0.272 mmol, 0.10 g) is suspended in 2 mL of DCM. DIEA (1.36 mmol, 0.236 mL) is added followed by methanesulfonyl chloride (0.543 mmol, 0.062 g) and the reaction is stirred at ambient temperature for 4 hrs. The solvent is removed under reduced pressure and the residue is redissolved and purified by HPLC to afford the title compound (21 mg, 23%); 1H NMR (DMSO-d6, 300 MHz) δ 7.80 (1H, d, J=2.6 Hz), 7.70 (1H, dd, J=2.5, 8.75 Hz), 7.45 (1H, d, J=8.87 Hz), 7.11 (1H, brt), 5.97 (1H, s), 4.28 (2H, t, J=6 Hz), 3.16 (2H, m), 2.91 (3H, s), 2.01 (2H, m); MS (ESI, Pos.) calcd for C13H14ClNO5S m/z [M+H]=332.0, found 331.9.

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionthe residue is redissolved
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-61a52d33cc63470fada6ee9163e4917a
Source dataset
uspto-grants-2009_05
Patent number
US07538233B2

Reaction notes

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