Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 135423127, compound

HRID 354201Notes

Reaction equation

HRID 354201 reaction equation
[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][N:5]1[C:26]([CH2:27][CH3:28])=[C:8]2[N:9]=[C:10]([C:14]3[C:15]([O:23][CH2:24][CH3:25])=[N:16][CH:17]=[C:18]([CH:22]=3)[C:19](O)=[O:20])[NH:11][C:12](=[O:13])[C:7]2=[N:6]1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC.Cl.[CH3:63][NH:64][O:65][CH3:66].C(=O)([O-])O.[Na+]>ClCCl>[CH3:29][N:2]([CH3:1])[CH2:3][CH2:4][N:5]1[C:26]([CH2:27][CH3:28])=[C:8]2[N:9]=[C:10]([C:14]3[C:15]([O:23][CH2:24][CH3:25])=[N:16][CH:17]=[C:18]([CH:22]=3)[C:19]([N:64]([O:65][CH3:66])[CH3:63])=[O:20])[NH:11][C:12](=[O:13])[C:7]2=[N:6]1

Participants

8

Reactant 6

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 135487616HCID 135487616, compound

Product 1

HCID 135423127HCID 135423127, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The title compound of Example 86 (710 mg, 1.8 mmol) was dissolved in dichloromethane (150 mL), 1-hydroxybenzotriazole hydrate (263 mg, 1.95 mmol), N,N-diisopropylethylamine (1.26 mL, 7 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (374 mg, 1.95 mmol) were added followed by N,O-dimethylhydroxylamine hydrochloride (173 mg, 1.8 mmol), and the resultant mixture stirred at room temperature for 14 h. Saturated aq. sodium hydrogen carbonate (80 mL) and dichloromethane (50 mL) were added, the organic phase removed and the aqueous phase extracted with dichloromethane (2×50 mL). The combined organic phases were dried over MgSO4, concentrated and purified by column chromatography (dichloromethane to 10% methanol in dichloromethane as eluant) to afford the title compound as a yellow oil (590 mg, 1.3 mmol).

Workup

  1. customthe organic phase removed
  2. extractionthe aqueous phase extracted with dichloromethane (2×50 mL)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. concentrationconcentrated
  5. custompurified by column chromatography (dichloromethane to 10% methanol in dichloromethane as eluant)

Sources & evidence

ORD record
ord-2236ed8316eb4eba80b5c1c08ad8020d
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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