Methylamine → HCID 59603097, compound

HRID 2068669Notes

Reaction equation

HRID 2068669 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=O)=[N:6][CH:7]=1.C1C=CC2N(O)N=[N:18][C:16]=2C=1.CCN=C=NCCCN(C)C.Cl.CN>C1COCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:18][CH3:16])=[O:11])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 46238459(5-Bromopyridin-2-yl)acetic acid

Product 1

HCID 59603097HCID 59603097, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-bromo-pyridin-2-yl-acetic acid (0.87 g, 4.0 mmol) in THF (12 mL) was added HOBt (0.74 g, 4.8 mmol) and EDCI.HCl (0.85 g, 4.4 mmol) and stirred the resulting reaction mixture for 15-20 min at room temperature followed by drop-wise addition of methyl amine (2.0 M in THF, 4.05 mL, 8.0 mmol). The resulting mixture was then continued to stir for 6-7 h at room temperature. After completion of reaction, water was added and extracted with ethyl acetate. The crude residue was purified over silica (60-120 M) using dichloromethane:methanol (97.5:2.5) to obtain the pale-yellow solid compound (0.25 g, 27%). 1H NMR (DMSO-d6, 400 MHz): δ 2.58 (d, J=4.8 Hz, 3H), 3.57 (s, 2H), 7.33 (d, J=1H), 7.96 (d, J=2.4 Hz & 8.4 Hz, 1H), 8.00 (br s, 1H) and 8.58 (d, J=2.4 Hz, 1H). MS: 229.11 (M+H+).

Workup

  1. customthe resulting reaction mixture for 15-20 min at room temperature
  2. stirringto stir for 6-7 h at room temperature
  3. additionwas added
  4. extractionextracted with ethyl acetate
  5. customThe crude residue was purified over silica (60-120 M)

Sources & evidence

ORD record
ord-357a1d5ea41a454ab31b1a16fc4cd469
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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