Hydrochloric Acid → HCID 67979500, compound

HRID 539330Notes

Reaction equation

HRID 539330 reaction equation
Cl.[CH:2]1([C:5]#[C:6][C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[CH2:12][C:11]2([CH2:20][CH2:19][CH:18]([O:21][CH3:22])[CH2:17][CH2:16]2)[C:10]3=[N:23]S(C(C)(C)C)=O)[CH2:4][CH2:3]1>O1CCOCC1>[CH:2]1([C:5]#[C:6][C:7]2[CH:8]=[C:9]3[C:13]([CH2:12][C:11]4([CH2:20][CH2:19][CH:18]([O:21][CH3:22])[CH2:17][CH2:16]4)[C:10]3=[NH:23])=[CH:14][CH:15]=2)[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67979718HCID 67979718, compound

Product 1

HCID 67979500HCID 67979500, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4 M HCl in dioxane (1.5 mL, 6.00 mmol) was added to a solution of N-(5′-(cyclopropylethynyl)-4-methoxyspiro[cyclohexane-1,2′-indene]-3′(1′H)-ylidene)-2-methylpropane-2-sulfinamide (Example 20i Step 2, 470 mg, 1.18 mmol) in dry dioxane (5 mL) at 5° C. The reaction mixture was allowed to come to r.t. and stirred for 1 h, then it was stored at 0° C. overnight and then concentrated. The product (as the hydrochloride salt) was dissolved in DCM and washed with aq. sat. NaHCO3, dried over Na2SO4 and concentrated to give 363 mg of the title compound (quantitative yield). 1 H NMR (500 MHz, CDCl3) δ ppm 0.78-0.85 (m, 2 H), 0.85-0.91 (m, 2 H), 1.34-1.49 (m, 3 H), 1.54-1.63 (m, 2 H), 1.68-1.84 (m, 2 H), 2.08-2.19 (m, 2 H), 2.98 (s, 2 H), 3.23-3.33 (m, 1 H), 3.38-3.43 (m, 3 H), 7.27 (m, 2 H), 7.46 (dd, 1 H), 7.69 (br. s., 1 H). MS (ES+) m/z 294 [M+H]+.

Workup

  1. customto come to r.t.
  2. waitit was stored at 0° C. overnight
  3. concentrationconcentrated
  4. dissolutionThe product (as the hydrochloride salt) was dissolved in DCM
  5. washwashed with aq. sat. NaHCO3
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fefaa1d7e26e4a5794feb974864924ec
Source dataset
uspto-grants-2014_10
Patent number
US08865911B2

Reaction notes

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