Dichloromethane → HCID 86719970, compound

HRID 1617330Notes

Reaction equation

HRID 1617330 reaction equation
FC(F)(F)C(O)=O.O[C:9]([C:22]1[CH:34]=[CH:33][C:25]2[N:26]([CH2:30][O:31][CH3:32])[C:27](=[O:29])[S:28][C:24]=2[CH:23]=1)([C:11]1[N:15](C2CCCCO2)[N:14]=[CH:13][CH:12]=1)[CH3:10].C(Cl)Cl>>[CH3:32][O:31][CH2:30][N:26]1[C:25]2[CH:33]=[CH:34][C:22]([C:9]([C:11]3[NH:15][N:14]=[CH:13][CH:12]=3)=[CH2:10])=[CH:23][C:24]=2[S:28][C:27]1=[O:29]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86719969HCID 86719969, compound

Product 1

HCID 86719970HCID 86719970, compoundYield 92%

Procedure

Add trifluoroacetic acid (20 Eq (molar), 2.26 moles, 170 mL) to a solution of 6-[1-hydroxy-1-(1-tetrahydropyran-2-yl-1H-pyrazol-5-yl)ethyl]-3-(methoxymethyl)-3H-1,3-benzothiazol-2-one (44 g, 113 mmoles) in DCM (0.2 M, 8.81 moles, 565 mL) and stirr at room temperature over night (˜16 hr.). Concentrate the resulting dark purple reaction mixture, dissolve it in EtOAc (2 L) and neutralize the solution by slowly adding saturated aqueous sodium bicarbonate. Transfer to a separatory funnel and extract into EtOAc, wash with water (300 mL) and then brine (300 mL). Dry over Na2SO4, filter, and concentrate. Purify the material by HPLC, eluting with EtOAc/Hexanes (1:1) to give 3-(methoxymethyl)-6-[1-(1H-pyrazol-5-yl)ethenyl]-3H-1,3-benzothiazol-2-one (30 g, 104 mmoles, 92% yield) as a thick yellow oil. LCMS (Low) desired product peak at rt=1.82 min., M+1=288.

Workup

  1. waitstirr at room temperature over night
  2. custom(˜16 hr.)
  3. concentrationConcentrate the resulting dark purple reaction mixture
  4. dissolutiondissolve it in EtOAc (2 L)
  5. extractionTransfer to a separatory funnel and extract into EtOAc
  6. washwash with water (300 mL)
  7. dry with materialDry over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate
  10. customPurify the material by HPLC
  11. washeluting with EtOAc/Hexanes (1:1)

Sources & evidence

ORD record
ord-ab097499eff2489085500c69c176f3d1
Source dataset
uspto-grants-2014_07
Patent number
US08765960B2

Reaction notes

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