Methylamine → HCID 89600830, compound

HRID 514207Notes

Reaction equation

HRID 514207 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:10](=[O:29])[CH:11]([CH2:16][C:17]3[N:22]=[C:21](S(C)(=O)=O)[C:20]([C:27]#[N:28])=[CH:19][CH:18]=3)[CH2:12][C:13]=2[O:14][CH3:15])=[C:4]([CH3:30])[CH:3]=1.[CH3:31][NH2:32]>O1CCCC1>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:10](=[O:29])[CH:11]([CH2:16][C:17]3[N:22]=[C:21]([NH:32][CH3:31])[C:20]([C:27]#[N:28])=[CH:19][CH:18]=3)[CH2:12][C:13]=2[O:14][CH3:15])=[C:4]([CH3:30])[CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 117667660HCID 117667660, compound

Product 1

HCID 89600830HCID 89600830, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6-[[3-(4-bromo-2,6-dimethyl-phenyl)-4-methoxy-2-oxo-cyclopent-3-en-1-yl]methyl]-2-methylsulfonyl-pyridine-3-carbonitrile (2.043 mmol, 1 g) was added a solution of methylamine (5.1 ml of a 2M solution in tetrahydrofuran, 10.22 mmol). The reaction was stirred at room temperature for three hours and then concentrated under reduced pressure to give a brown gum. The crude product was purified by column chromatography on SiO2 using a hexane: EtOAc gradient to yield the desired compound (890 mg, 99%) as an orange solid. 1H NMR (400 MHz, CDCl3) (diagnostic peaks) δ ppm 7.55 (d, 1H), 7.18 (d, 2H), 6.45 (d, 1H), 3.55 (s, 3H), 3.05 (d, 3H), 2.15 (s, 3H), 2.00 (s, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give a brown gum
  3. customThe crude product was purified by column chromatography on SiO2 using a hexane

Sources & evidence

ORD record
ord-82f2d388003d42ed9fc3f0f0a418c0ac
Source dataset
uspto-grants-2015_08
Patent number
US09107415B2

Reaction notes

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