2-Methoxyethylamine → HCID 68544478, compound

HRID 2245546Notes

Reaction equation

HRID 2245546 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]([OH:13])=O)[CH:8]=2)[NH:3]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[CH3:56][O:57][CH2:58][CH2:59][NH2:60].C(=O)([O-])O.[Na+]>C(#N)C.CN(C)C=O>[CH3:56][O:57][CH2:58][CH2:59][NH:60][C:11]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2](=[O:1])[CH2:10]2)=[O:13]

Participants

8

Reactant 6

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27733182-Oxindole-5-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 68544478HCID 68544478, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

2-Oxoindoline-5-carboxylic acid (0.470 g, 2.66 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (1.010 g, 3.15 mmol), 1-hydroxybenzotriazole hydrate (0.417 g, 3.09 mmol) and N,N-diisopropylethylamine (0.7 mL, 4.0 mmol) were suspended in acetonitrile/N,N-dimethylformamide, (10 mL:2 mL), and stirred at room temperature for 30 min. 2-Methoxyethanamine (0.516 g, 6.88 mmol) was added and stirring was continued for 2 h. Saturated aqueous sodium hydrogencarbonate was added (10 mL) and the solvents were removed in vacuo. The residue was purified on a silica gel column using a gradient chloroform/methanol, (100:1 to 1:1), as the eluent to give 0.355 g (57% yield) of the title compound as a solid: 1H NMR (DMSO-d6, 400 MHz) δ 10.59 (s, 1H), 8.31 (m, 1H), 7.72 (d, J=7 Hz, 1H), 7.71 (s, 1H), 6.83 (d, J=8 Hz, 1H), 3.51 (s, 2H), 3.42 (m, 2H), 3.39 (m, 2H), 3.24 (s, 3H); MS (ES) m/z 235 (M++1).

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customthe solvents were removed in vacuo
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-cc49abd9f1444b45b12b286263c0667c
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

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