Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 59278382, compound

HRID 1361213Notes

Reaction equation

HRID 1361213 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[O:4][N:3]=1.F[P-](F)(F)(F)(F)F.[N:17]1([O:26][C:27](N(C)C)=[N+](C)C)[C:21]2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C.Cl.CNOC>CN(C=O)C.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH3:27][O:26][N:17]([CH3:21])[C:7]([C:5]1[O:4][N:3]=[C:2]([Br:1])[CH:6]=1)=[O:9]

Participants

8

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 3277163-Bromoisoxazole-5-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 59278382HCID 59278382, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-bromoisoxazole-5-carboxylic acid (2.85 g, 14.8 mmol) in DMF (74 mL) was added 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (6.89 g, 18.1 mmol). The solution was cooled (0° C.) and DIPEA (10.5 mL, 60.3 mmol) was added followed by N,O-dimethylhydroxylamine hydrochloride (1.81 g, 18.6 mmol) and the reaction was maintained at room temperature. After 25 hours, DMAP (183 mg, 1.50 mmol) was added. After 38 hours, the mixture was diluted with EtOAc and washed with saturated aqueous NaHCO3, saturated aqueous NH4Cl, water, brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with a gradient of 0%-100% EtOAc in heptane to afford 3-bromo-isoxazole-5-carboxylic acid methoxy-methyl-amide as a pale yellow solid. MS m/z 235 (M), 237 (M+2).

Workup

  1. additionwas added
  2. waitAfter 38 hours
  3. washwashed with saturated aqueous NaHCO3, saturated aqueous NH4Cl, water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with a gradient of 0%-100% EtOAc in heptane

Sources & evidence

ORD record
ord-71dd6f08008e403b871ab44b786b38c5
Source dataset
uspto-grants-2011_02
Patent number
US07879873B2

Reaction notes

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