Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 74347206, compound

HRID 18643Notes

Reaction equation

HRID 18643 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19](=[O:26])(=[O:25])[N:20]=[CH:21][N:22]([CH3:24])[CH3:23])=[CH:15][CH:14]=3)[C:11]([CH3:27])=[C:10]([C:28](Cl)=[O:29])[CH:9]=2)=[CH:4][CH:3]=1.Cl.[CH3:32][NH:33][O:34][CH3:35]>C(Cl)Cl>[CH3:35][O:34][N:33]([CH3:32])[C:28]([C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:12]([C:13]2[CH:14]=[CH:15][C:16]([S:19](=[O:25])(=[O:26])[N:20]=[CH:21][N:22]([CH3:24])[CH3:23])=[CH:17][CH:18]=2)[C:11]=1[CH3:27])=[O:29]

Participants

4

Reactant 2

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 74932797HCID 74932797, compound

Product 1

HCID 74347206HCID 74347206, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) mixture of Example 30A (1.9 g, 4.64 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.5 g, 5.11 mmol) in DCM (50 mL) was added TEA (1.62 mL, 11.6 mmol). The mixture was stirred at room temperature for five hours after which the solvents were removed under reduced pressure and the residue purified by chromatography using a mixture of DCM:methanol (95:5) to obtain the titled compound. 1H NMR (CDCl3) δ ppm 2.20 (3H), 2.47 (6H), 2.74 (3H), 3.39 (3H), 6.20 (1H), 7.33-7.42 (4H), 7.50-7.90 (5H); MS (ESI) m/z 489 (M+H).

Workup

  1. customwere removed under reduced pressure
  2. customthe residue purified by chromatography
  3. additiona mixture of DCM:methanol (95:5)

Sources & evidence

ORD record
ord-04bafb57b5a5458ca6dc5dcfdb64502a
Source dataset
uspto-grants-2010_06
Patent number
US07741364B2

Reaction notes

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