2-Methoxybenzylamine → HCID 68541546, compound

HRID 2245544Notes

Reaction equation

HRID 2245544 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.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C.[CH3:35][O:36][C:37]1[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=1[CH2:39][NH2:40]>CN(C)C=O.C(#N)C>[CH3:35][O:36][C:37]1[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=1[CH2:39][NH:40][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

6

Reactant 4

HCID 812922-MethoxybenzylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27733182-Oxindole-5-carboxylic acid

Product 1

HCID 68541546HCID 68541546, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

To a solution of 2-oxoindoline-5-carboxylic acid (0.200 g, 1.12 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.477 g, 2.47 mmol), diisopropylethylamine (0.586 mL, 3.37 mmol) and catalytic amount of N,N-dimethylaminopyridine in N,N-dimethylformamide/acteonitrile (1:1, 4 mL) was added 2-methoxybenzylamine (0.295 mL, 2.26 mmol) and the reaction mixture stirred at room temperature for 1 h. The solvent was evaporated and the crude material was purified on a short silica gel column using dichloromethane containing 5% methanol as the eluent. This was followed by triturating from ethyl acetate to give 0.10 g (33% yield) of the yellow title compound: 1H NMR (DMSO-d6, 400 MHz) δ 10.60 (br s, 1H), 8.65 (t, J=6 Hz, 1H), 7.79-7.77 (m, 2H), 7.21 (t, J=8 Hz, 1H), 7.15 (d, J=8 Hz, 1H), 6.98 (d, J=8 Hz, 1H), 6.90-6.84 (m, 2H), 4.42 (d, J=6 Hz, 2H), 3.81 (s, 3H), 3.53 (s, 2H); MS (ES) m/z 297 (M++1), m/z 295 (M−−1).

Workup

  1. customThe solvent was evaporated
  2. customthe crude material was purified on a short silica gel column
  3. customby triturating from ethyl acetate

Sources & evidence

ORD record
ord-976dacfef08842039919418b10048769
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

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