Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 88414359, compound

HRID 1963086Notes

Reaction equation

HRID 1963086 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:20]3[N:21]=[CH:22][C:23]([C:25]([OH:27])=O)=[CH:24][C:19]3=[C:18]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:17]=2[CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[C:36]=2[CH3:42])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:44][NH:45][O:46][CH3:47].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:20]3[N:21]=[CH:22][C:23]([C:25](=[O:27])[N:45]([O:46][CH3:47])[CH3:44])=[CH:24][C:19]3=[C:18]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:17]=2[CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[C:36]=2[CH3:42])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 70663716HCID 70663716, compound

Product 1

HCID 88414359HCID 88414359, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the compound of example 8, step 11 (1.002 g, 1.75 mmol), N,O-dimethylhydroxylamine hydrochloride (0.213 g, 2.19 mmol), EDIA (0.76 ml, 4.38 mmol) and TBTU (0.702 g, 2.19 mmol) in 15 ml of anhydrous DCM was stirred at room temperature for 4 h. DCM (15 ml) was then added and the solution was washed with 0.5 N hydrochloric acid (30 ml), a saturated solution of sodium hydrogencarbonate (15 ml) and brine (15 ml), dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane/EA, 50:50, then 40:60, then 35:65) to give 0.99 g of the title compound as a yellow oil.

Workup

  1. washthe solution was washed with 0.5 N hydrochloric acid (30 ml)
  2. dry with materiala saturated solution of sodium hydrogencarbonate (15 ml) and brine (15 ml), dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (cyclohexane/EA, 50:50

Sources & evidence

ORD record
ord-2a14668604c14fddbf01adc727491152
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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