5-(benzyloxy)-2-(4-fluorophenyl)-N-methylfuro[2,3-c]pyridine-3-carboxamide → HCID 178485250、化合物

HRID 44067ノート

反応式

HRID 44067 の反応式
C([O:8][C:9]1[CH:10]=[C:11]2[C:17]([C:18]([NH:20][CH3:21])=[O:19])=[C:16]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[O:15][C:12]2=[CH:13][N:14]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[F:28][C:25]1[CH:24]=[CH:23][C:22]([C:16]2[O:15][C:12]3=[CH:13][N:14]=[C:9]([OH:8])[CH:10]=[C:11]3[C:17]=2[C:18]([NH:20][CH3:21])=[O:19])=[CH:27][CH:26]=1

参加物

4

反応物 1

HCID 672175935-(benzyloxy)-2-(4-fluorophenyl)-N-methylfuro[2,3-c]pyridine-3-carboxamide

生成物 1

HCID 178485250HCID 178485250、化合物収率 91.4%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Pd/C (178 mg, 0.084 mmol) (10%; 50% wet) was added to a stirring solution of 5-(benzyloxy)-2-(4-fluorophenyl)-N-methylfuro[2,3-c]pyridine-3-carboxamide (630 mg, 1.674 mmol) in THF (83 ml) at room temperature. It was placed under an atmosphere of H2 and allowed to stir for 20 minutes after which a precipitate had formed. The reaction was purged with N2 and diluted with MeOH until all solids had dissolved. The mixture was filtered through a pad of celite washing with MeOH and the filtrate was concentrated to give the expected product 2-(4-fluorophenyl)-5-hydroxy-N-methylfuro[2,3-c]pyridine-3-carboxamide (460 mg, 1.53 mmol, 91% yield) consistent by LCMS and NMR. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.30-8.40 (2H, m), 7.98 (2H, dd, J=8.78, 5.77 Hz), 7.35-7.45 (3H, m), 6.61 (1H, s), 2.81 (3H, d, J=4.52 Hz). LC-MS retention time: 0.847 min; m/z (MH+): 287. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters SunFire 5u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% acetonitrile/90% H2O/0.1% trifluoroacetic acid and solvent B was 10% H2O/90% acetonitrile/0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode.

後処理

  1. customhad formed
  2. customThe reaction was purged with N2
  3. additiondiluted with MeOH until all solids
  4. dissolutionhad dissolved
  5. filtrationThe mixture was filtered through a pad of celite
  6. washwashing with MeOH
  7. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-e02b9cdfa59e42169c572f107db18201
出典データセット
uspto-grants-2013_09
特許番号
US08536338B2

反応ノート

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