Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 118451628, compound

HRID 63705Notes

Reaction equation

HRID 63705 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:41][C:42]([OH:45])([CH3:44])[CH3:43])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([C:17](O)=[O:18])=[CH:12][C:11]=3[N:10]=[C:9]([NH:20][C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:8]=2[N:40]=1)[CH3:2].CN([C:49]([O:53][N:54]1N=NC2C=CC=C[C:55]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.CNOC>CN(C=O)C>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:41][C:42]([OH:45])([CH3:43])[CH3:44])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([C:17]([N:54]([O:53][CH3:49])[CH3:55])=[O:18])=[CH:12][C:11]=3[N:10]=[C:9]([NH:20][C:21]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:8]=2[N:40]=1)[CH3:2]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118451601HCID 118451601, compound

Product 1

HCID 118451628HCID 118451628, compoundYield 111.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-4-(tritylamino)-1H-imidazo[4,5-c]quinoline-7-carboxylic acid (484 mg, 741 μmol) in DMF (5.19 mL) in an inert atmosphere was added TBTU (357 mg, 1.11 mmol), DIEA (388 μL, 2.22 mmol) and N,O-dimethylhydroxylamine hydrochloride (108 mg, 1.11 mmol) with stirring. The reaction mixture was stirred for 1 h at room temperature and afterwards the mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate (40 mL, 2×20 mL) and water (40 mL). The organic phases were washed with water (2×20 mL), combined, dried over MgSO4, concentrated in vacuo and purified by flash chromatography (silica gel, 50% to 100% ethyl acetate in heptane) to give the title compound (0.53 g, quant.) as white foam; LC-MS (UV peak area, ESI) 92%, 644.4 (MH+).

Workup

  1. stirringThe reaction mixture was stirred for 1 h at room temperature
  2. concentrationafterwards the mixture was concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate (40 mL, 2×20 mL) and water (40 mL)
  4. washThe organic phases were washed with water (2×20 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography (silica gel, 50% to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-b97ff5d046064517b4402565e29dbce0
Source dataset
uspto-grants-2016_09
Patent number
US09447097B2

Reaction notes

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