N,O-Dimethylhydroxylamine → HCID 86607369, compound

HRID 1428986Notes

Reaction equation

HRID 1428986 reaction equation
[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=O)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.CN([C:29]([O:33][N:34]1N=NC2C=CC=C[C:35]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CONC>C(#N)C>[CH3:29][O:33][N:34]([CH3:35])[C:14]([C:11]1[N:10]=[CH:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:12]=1[CH3:13])=[O:16]

Participants

6

Reactant 4

HCID 14232N,O-DimethylhydroxylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 538968611-Benzyl-5-methyl-1H-imidazole-4-carboxylic acid

Product 1

HCID 86607369HCID 86607369, compoundYield 134%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Part B: To a magnetically stirred solution of N-benzyl-5-methyl-1H-imidazole-4-carboxylic acid (6.77 gram, 0.031 mol) in anhydrous acetonitrile (35 ml) was successively added diisopropylethylamine (DIPEA) (17.2 ml, 0.0992 mol), HBTU (14.098 gram, 0.0372 mol) and methoxy-methylamine (3.63 gram, 0.0372 mol). The resulting mixture was reacted at 20° C. for 16 hours and subsequently concentrated in vacuo. The resulting residue was taken up in ethylacetate and successively washed with 5% aqueous NaHCO3 solution and water. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The resulting oily residue (18.45 gram) was purified by flash chromatography (ethyl acetate/acetone=7/3 (v/v)) to give N-methoxy-N-methyl-5-methyl-1-benzyl-1H-imidazole-4-carboxamide (10.77 gram, 82% yield). MH+=260. 1H-NMR (400 MHz, CDCl3): 2.34 (s, 3H), 3.47 (s, 3H), 3.77 (s, 3H), (s, 2H), 7.05-7.10 (m, 2H), 7.18-7.28 (m, 3H), 7.48 (s, 1H).

Workup

  1. customThe resulting mixture was reacted at 20° C. for 16 hours
  2. concentrationsubsequently concentrated in vacuo
  3. washsuccessively washed with 5% aqueous NaHCO3 solution and water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting oily residue (18.45 gram) was purified by flash chromatography (ethyl acetate/acetone=7/3 (v/v))

Sources & evidence

ORD record
ord-f06c86c78b3e49b3b60f32c70fed0ac0
Source dataset
uspto-grants-2015_01
Patent number
US08937184B2

Reaction notes

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