Methylamine → HCID 10214443, compound

HRID 1615224Notes

Reaction equation

HRID 1615224 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.[CH3:14][N:15](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=C2N=NN(O)C2=CC=1.O.CCN(C(C)C)C(C)C.CN>C1COCC1.CN(C=O)C>[CH3:14][NH:15][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 5

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27733182-Oxindole-5-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 10214443HCID 10214443, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

An oven-dried round-bottom flask was charged with 2-oxoindoline-5-carboxylic acid (89 mg, 0.500 mmol), TBTU (193 mg, 0.600 mmol), HOBt hydrate (81 mg, 0.600 mmol), DIPEA (0.13 mL, 0.750 mmol) and DMF (3.0 mL) and stirred for 5 minutes. Methyl amine (0.75 mL of a 2.0 M solution in THF) was then added and reaction was stirred for 4 hours at which time NaHCO3(sat) (2 mL) was added. Solvents were removed in vacuo and the residue was purified by column chromatography (silica gel, 92:8 CH2Cl2/MeOH) to give the title compound (11 mg, 12%). 1H NMR (400 MHz, CD3OD) δ ppm 7.69-7.75 (m, 2H), 6.94 (d, J=8.1 Hz, 1H), 3.58 (s, 2H), 2.97 (s, 3H); MS ESI 191.0 [M+H]+, calcd for [C10H10N2O2+H]+ 191.08.

Workup

  1. customreaction
  2. additionwas added
  3. customSolvents were removed in vacuo
  4. customthe residue was purified by column chromatography (silica gel, 92:8 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-865ce43e1c54442d86bc8efd58f40885
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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