Hydrochloric Acid → HCID 86706698, compound

HRID 1468086Notes

Reaction equation

HRID 1468086 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[F:12])[CH2:8][C:7]1([CH2:17][CH2:16][CH:15]([O:18][CH3:19])[CH2:14][CH2:13]1)[C:6]2=[N:20]S(C(C)(C)C)=O.CCOCC>O1CCOCC1>[Br:2][C:3]1[CH:4]=[C:5]2[C:9]([CH2:8][C:7]3([CH2:17][CH2:16][CH:15]([O:18][CH3:19])[CH2:14][CH2:13]3)[C:6]2=[NH:20])=[CH:10][C:11]=1[F:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86706697HCID 86706697, compound2×

Product 1

HCID 86706698HCID 86706698, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

HCl (4 M in 1,4-dioxane) (7.84 mL, 31.4 mmol) was added to a solution of N-(5′-bromo-6′-fluoro-4-methoxyspiro[cyclohexane-1,2′-indene]-3′(1′H)-ylidene)-2-methylpropane-2-sulfinamide (Intermediate 12, 1.35 g, 3.14 mmol) in anhydrous 1,4-dioxane (23 mL) and the resulting mixture was stirred under an argon atmosphere for 15 min. Et2O (60 mL) was added and the precipitate was filtered off and washed with Et2O, then partitioned between DCM and saturated aqueous NaHCO3. The phases were separated, the organic phase dried over sodium sulfate and concentrated to give the title compound (0.95 g, 93% yield) that was used without further purification. MS (ES+) m/z 326, 328 [M+H]+.

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with Et2O
  3. custompartitioned between DCM and saturated aqueous NaHCO3
  4. customThe phases were separated
  5. dry with materialthe organic phase dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ca2408efc04a461ba8724a8ad3180223
Source dataset
uspto-grants-2015_04
Patent number
US09000183B2

Reaction notes

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