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

HRID 1913387Notes

Reaction equation

HRID 1913387 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-644c2928345a4e189fe50bf35f6e6270
Source dataset
uspto-grants-2013_12
Patent number
US08609713B2

Reaction notes

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