Hydrochloric Acid → HCID 86706696, compound

HRID 1468084Notes

Reaction equation

HRID 1468084 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[CH3:12])[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>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[CH3:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86706695HCID 86706695, compound2×

Product 1

HCID 86706696HCID 86706696, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

HCl-solution (4 M in 1,4-dioxane, 4.76 mL, 19.0 mmol) was added to a solution of N-(5′-bromo-4-methoxy-6′-methylspiro[cyclohexane-1,2′-indene]-3′(1′H)-ylidene)-2-methylpropane-2-sulfinamide (Intermediate 9, 812 mg, 1.90 mmol) in anhydrous 1,4-dioxane (8 mL). The resulting mixture was stirred under a nitrogen atmosphere at r.t. for 1 h. The mixture was concentrated and the residue was dissolved in a small amount of DCM (˜4-6 mL). Et2O (14 mL) was added and the solid was filtered off and washed with Et2O. The solid was partitioned between DCM (10 mL) and saturated aqueous NaHCO3 (8 mL). The phases were separated and the organic layer concentrated. The product (446 mg) was used directly in the next step: MS (EI) m/z 321, 323 [M+.].

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in a small amount of DCM (˜4-6 mL)
  3. additionEt2O (14 mL) was added
  4. filtrationthe solid was filtered off
  5. washwashed with Et2O
  6. customThe solid was partitioned between DCM (10 mL) and saturated aqueous NaHCO3 (8 mL)
  7. customThe phases were separated
  8. concentrationthe organic layer concentrated

Sources & evidence

ORD record
ord-ef6b35789ab14da8ab1b6b529df06b65
Source dataset
uspto-grants-2015_04
Patent number
US09000183B2

Reaction notes

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