Pyridine → HCID 136386024, compound

HRID 351908Notes

Reaction equation

HRID 351908 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:19]2[C:18](=O)[CH2:17][CH2:16][CH2:15][C:14]=2[NH:13][CH:12]=1)=[O:10].N1C=CC=CC=1.Cl.[O:28]([NH2:30])[CH3:29]>CCO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:19]2[C:18](=[N:30][O:28][CH3:29])[CH2:17][CH2:16][CH2:15][C:14]=2[NH:13][CH:12]=1)=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 22714681HCID 22714681, compound

Product 1

HCID 136386024HCID 136386024, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (2-fluoro-phenyl)-amide (0.73 mmol), pyridine (2.2 mmol), EtOH (10 ml) and methoxylamine hydrochloride (2.2 mmol) are combined in a sealed tube and heated at 120° C. for 16 hours. The reaction mixture is cooled to room temperature, the solvent is removed in vacuo and the residue is treated with 10 ml of H2O for 5 minutes. The resulting solid is collected by vacuum filtration to yield 160 mg (72%) of 4-methoxyimino-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (2-fluoro-phenyl)-amide as a white solid. 1H NMR (DMSO-d6) δ1.80-1.86 (m, 2H), 2.62-2.73 (m, 4H), 3.81 (s, 3H), 7.10-7.29 (m, 3H), 7.48 (d, 1H), 8.01 (t, 1H), 11.70 (s, 1H), 11.81 (s, 1H).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe solvent is removed in vacuo
  3. additionthe residue is treated with 10 ml of H2O for 5 minutes
  4. filtrationThe resulting solid is collected by vacuum filtration

Sources & evidence

ORD record
ord-ad7283a785874f17aa38992b2a815442
Source dataset
uspto-grants-2004_06
Patent number
US06743817B2

Reaction notes

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