Water → HCID 131730703, compound

HRID 448024Notes

Reaction equation

HRID 448024 reaction equation
[CH2:1]([N:5]1[CH:9]=[C:8]([CH:10]=O)[S:7]/[C:6]/1=[CH:12]\[C:13]([C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])=[O:14])[CH2:2][CH2:3][CH3:4].[OH2:24].[N:25]1C=CC=CC=1>>[CH2:1]([N:5]1[CH:9]=[C:8]([CH:10]=[N:25][OH:24])[S:7]/[C:6]/1=[CH:12]\[C:13]([C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])=[O:14])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 24954261HCID 24954261, compound

Product 1

HCID 131730703HCID 131730703, compound

Procedure

A mixture of Example 19 (35 mg, 0.1 mmol) and NH2OH_HCl (10 mg, 0.15 mmol) in pyridine (2 mL) was stirred at room temperature for 14 hours. The mixture was poured into water and extracted with ethyl acetate (2×15 mL). The combined organic extracts were washed sequentially with water and brine, dried over MgSO4, Filtered, and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate as an eluent to provide the title compounds as a mixture of E and Z isomers. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.90 (t, J=7.3 Hz, 3 H), 1.25-1.42 (m, 2 H), 1.73 (m, 2 H), 3.86 (s, 3 H), 4.01 (m, 2 H), 6.58 (s, 0.6 H), 6.64 (s, 0.4 H), 7.04-7.20 (m, 1H), 7.35-7.49 (m, 1 H), 7.57 (s, 1 H), 7.61-7.70 (m, 1 H), 7.88 (s, 0.6 H), 8.19 (s, 0.4H), 11.26 (s, 0.4 H), 11.72 (s, 0.6 H), MS (DCI) m/z 368 (M+H)+, 352 (M+H-16)+.

Workup

  1. extractionextracted with ethyl acetate (2×15 mL)
  2. washThe combined organic extracts were washed sequentially with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationFiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-39630052b22b404db2cf144314a5bc20
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

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