Methanesulfonyl chloride → HCID 86707735, compound

HRID 1190843Notes

Reaction equation

HRID 1190843 reaction equation
[C:1]1([C:7]2[CH:21]=[CH:20][C:10]3[N:11]=[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:13][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCN2C(=NCCC2)CC1.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>CN(C=O)C.O>[CH3:33][S:34]([CH:14]([C:12]1[S:13][C:9]2[CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:21]=[CH:20][C:10]=2[N:11]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:36])=[O:35]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chloride2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58470454HCID 58470454, compound

Product 1

HCID 86707735HCID 86707735, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 2-(6-phenylbenzo[d]thiazol-2-yl)acetate (390 mg, 1.3 mmol) (described in WO 2011/074560) in DMF (4 mL) at 0° C. was added DBU (0.49 mL, 3.3 mmol) and the reaction mixture was stirred at rt for 10 min. Methanesulfonyl chloride (0.12 mL, 1.6 mmol) was added dropwise and the mixture stirred for 0.5 h. Additional methanesulfonyl chloride (0.030 mL, 0.40 mmol) was added and the reaction mixture stirred for 10 min. The reaction mixture was diluted with H2O then extracted with EtOAc (3×), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0 to 100% EtOAc/hexane to give Compound 89a (360 mg, 73% yield) as yellow powder. RT=2.06 min using analytical method (Q), 376.9 (M+H). 1H NMR (500 MHz, CDCl3) δ 7.88-7.75 (m, 1H), 7.68-7.53 (m, 3H), 7.53-7.34 (m, 5H), 4.42 (qd, J=7.2, 3.0 Hz, 2H), 3.39-3.21 (m, 3H).

Workup

  1. stirringthe mixture stirred for 0.5 h
  2. stirringthe reaction mixture stirred for 10 min
  3. extractionthen extracted with EtOAc (3×)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 0 to 100% EtOAc/hexane

Sources & evidence

ORD record
ord-e219881acf034d5f9a1c8da0f3a69184
Source dataset
uspto-grants-2014_03
Patent number
US08680090B2

Reaction notes

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