Hydrochloric Acid → HCID 136386516, compound

HRID 1821902Notes

Reaction equation

HRID 1821902 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[NH:19][C:14]3=[CH:15][N:16]=[CH:17][CH:18]=[C:13]3[CH:12]=2)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:20]([O:24][C:25](=[O:31])[NH:26][CH2:27][CH2:28][O:29][NH2:30])([CH3:23])([CH3:22])[CH3:21].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[N:30][O:29][CH2:28][CH2:27][NH:26][C:25](=[O:31])[O:24][C:20]([CH3:22])([CH3:21])[CH3:23])[C:11]2[NH:19][C:14]3=[CH:15][N:16]=[CH:17][CH:18]=[C:13]3[CH:12]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15610443tert-butyl N-(2-(aminooxy)ethyl)carbamateHCID 57893562HCID 57893562, compound

Product 1

HCID 136386516HCID 136386516, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(3,4-Dichlorophenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (Example 127) (92 mg, 0.32 mmol) and tert-butyl[2-(aminooxy)ethyl]carbamate (58 mg, 0.33 mmol) were combined in ethanol (5 mL). The pH was adjusted to ca. 4 using 1 M ethereal hydrogen chloride and the react ion mixture was refluxed for 14 h. The solvent was removed under vacuum. The residue was dissolved in ethyl acetate, washed with saturated sodium bicarbonate solution and then brine, dried over sodium sulfate, and concentrated to a solid. Purification by Biotage chromatography (silica gel, 97:3 CH2Cl2:CH3OH) produced tert-butyl 2-[[[(3,4-dichlorophenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethylcarbamate (74 mg, 51%) as a yellow foam: 1H NMR (300 MHz CD3OD) δ 1.39 (9H, s), 3.50-3.54 (2H, m), 4.26-4.39 (2H, m), 6.35 (0.35H, s), 6.62 (0.65H, s), 7.38-7.77 (4H, m), 8.04-8.11 (1H, m), 8.72 (0.35H, s), 8.93 (0.65H, s); ESI MS m/z 449 [C21H22Cl2N4O3+H]+.

Workup

  1. temperaturethe react ion mixture was refluxed for 14 h
  2. customThe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate solution
  5. dry with materialbrine, dried over sodium sulfate
  6. concentrationconcentrated to a solid
  7. customPurification by Biotage chromatography (silica gel, 97:3 CH2Cl2:CH3OH)

Sources & evidence

ORD record
ord-56bca05161704120bfa93c25dd1b3433
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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