Hydrochloric Acid → HCID 67979559, compound

HRID 1770982Notes

Reaction equation

HRID 1770982 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:22][CH2:21][C:20]4(OCC[O:23]4)[CH2:19][CH2:18]3)[C:8]2=[N:11]S(C(C)(C)C)=O)=[CH:4][CH:3]=1.Cl>O1CCOCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]3)[C:8]2=[NH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67979386HCID 67979386, compound

Product 1

HCID 67979559HCID 67979559, compoundYield 115.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To N-(6″-bromodispiro[1,3-dioxolane-2,1′-cyclohexane-4′,2″-inden]-1″(3″H)-ylidene)-2-methylpropane-2-sulfinamide (Example 115, Step 1, 288 mg, 0.65 mmol) in 1,4-dioxane (2 mL) under N2 (g) was added HCl (4 M in 1,4-dioxane, 1.635 mL, 6.54 mmol). The mixture was stirred at r.t overnight and was then concentrated. The crude product was dissolved in DCM and was washed with NaHCO3 (sat. aq). The aqueous phase was extracted with DCM. The combined organics were dried using a phase separator and concentrated to give the title compound (220 mg, quantitative yield) that was used directly in the next step: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.13-1.24 (m, 2H) 1.25-1.35 (m, 2H) 1.66-1.75 (m, 2H) 1.83-1.93 (m, 2H) 2.86 (s, 2H) 5.83 (s, 1H) 7.40 (d, 1H) 7.64 (dd, 1H) 7.69 (d, 1H); MS (ES+) m/z 292 [M+H]+.

Workup

  1. concentrationwas then concentrated
  2. dissolutionThe crude product was dissolved in DCM
  3. washwas washed with NaHCO3 (sat. aq)
  4. extractionThe aqueous phase was extracted with DCM
  5. customThe combined organics were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-67e9ceb659b84984b029f94f5d56b3df
Source dataset
uspto-grants-2016_02
Patent number
US09248129B2

Reaction notes

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