Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 87522359, compound

HRID 514661Notes

Reaction equation

HRID 514661 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[C:10](\[CH3:14])/[C:11](O)=[O:12])[CH:5]=[CH:6][C:7]=1[F:8].Cl.[CH3:16][NH:17][O:18][CH3:19].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[C:10](\[CH3:14])/[C:11]([N:17]([O:18][CH3:19])[CH3:16])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

8

Reactant 5

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68628071HCID 68628071, compound

Product 1

HCID 87522359HCID 87522359, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 9B (11.9 g, 55.45 mmol), N,O-dimethylhydroxylamine hydrochloride (5.7 g, 58 mmol), 1-hydroxybenzotriazole hydrate (7.88 g, 53.8 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (11 g, 57.58 mmol) and diisopropylethyl amine (47.4 g, 63.9 mL, 370 mol) was stirred in DMF (400 mL) at ambient temperature overnight. The solution was diluted with water and extracted with ethyl acetate. The combined organic extract was washed with saturated sodium bicarbonate solution, 1N HCl, water, brine, dried over Na2SO4, filtered, and evaporated in vacuo. The resulting material was chromatographed (SiO2, 20% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) to leave the title compound (6.85 g, 48% yield). 1H NMR (300 MHz, CDCl3) δ ppm 7.39 (dd, J=7.12, 2.37 Hz, 1H), 7.10-7.21 (m, 2H), 6.71 (s, 1H), 3.69 (s, 3H), 3.28 (s, 3H), 2.10 (s, 3H). MS (DCI+) 258 (M+H).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe combined organic extract
  3. washwas washed with saturated sodium bicarbonate solution, 1N HCl, water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe resulting material was chromatographed (SiO2, 20% ethyl acetate/hexanes to 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4f77dceba3194032bcc9d565309ec45c
Source dataset
uspto-grants-2015_08
Patent number
US09108905B2

Reaction notes

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