Water → HCID 71611916, compound

HRID 1048739Notes

Reaction equation

HRID 1048739 reaction equation
COC[O:4][C:5]1[CH:6]=[C:7]([CH2:17][N:18]([CH:28]([CH3:30])[CH3:29])[S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)(=[O:21])=[O:20])[CH:8]=[C:9]2[C:14]=1[O:13][C:12]([CH3:16])([CH3:15])[CH:11]=[CH:10]2.O>O1CCCC1.Cl>[OH:4][C:5]1[CH:6]=[C:7]([CH2:17][N:18]([CH:28]([CH3:30])[CH3:29])[S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)(=[O:21])=[O:20])[CH:8]=[C:9]2[C:14]=1[O:13][C:12]([CH3:15])([CH3:16])[CH:11]=[CH:10]2

Participants

5

Reactant 2

HCID 962WaterHCID 86688384HCID 86688384, compound

Product 1

HCID 71611916HCID 71611916, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-[(8-Methoxymethoxy-2,2-dimethyl-2H-chromen-6-yl)methyl]-N-(propan-2-yl)pyridine-2-sulfonamide (31 mg, 0.07 mmol) was dissolved in a cosolvent of tetrahydrofuran (1 mL) and 6 N aqueous HCl (1 mL), and the reaction stirred for 3 h. Ten milliliters of water was added to the reaction mixture, and then tetrahydrofuran was evaporated. The remaining aqueous phase was extracted by methylene chloride (10 mL×3), washed with brine, dried with anhydrous magnesium sulfate, and concentrated in vacuo. 6h (19 mg, 49%) was purified by silica gel chromatography with ethyl acetate/hexane (1/1). 1H NMR (CDCl3): δ 0.77 (d, J=6.45 Hz, 6H), 1.44 (s, 6H), 1.72-1.79 (m, 1H), 3.11 (d, J=7.62 Hz, 2H), 4.39 (s, 2H), 5.61 (d, J=9.67 Hz, 1H), 6.25 (d, J=9.96 Hz, 1H), 6.50 (d, J=1.76 Hz, 1H), 6.65 (d, J=1.76 Hz, 1H), 7.43-7.47 (m, 1H), 7.84-7.97 (m, 2H), 8.69 (d, J=4.40 Hz, 1H). HRMS (m/z): [M+Na]+ calcd 425.15055, found 425.15091. HPLC-1: flow rate 2 mL/min, tR=2.9 min, purity=100%; flow rate 1 mL/min, tR=5.6 min, purity=100%. HPLC-2: tR=5.172 min, purity=100%.

Workup

  1. customtetrahydrofuran was evaporated
  2. extractionThe remaining aqueous phase was extracted by methylene chloride (10 mL×3)
  3. washwashed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. custom6h (19 mg, 49%) was purified by silica gel chromatography with ethyl acetate/hexane (1/1)

Sources & evidence

ORD record
ord-67601c564a87466985cde7907d0df41e
Source dataset
uspto-grants-2016_07
Patent number
US09381260B2

Reaction notes

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