Phenethylamine → HCID 89837825、化合物

HRID 1749007ノート

反応式

HRID 1749007 の反応式
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([NH:12][C:13](=O)[CH2:14][CH3:15])[CH:3]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[CH2:39]([NH2:47])[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6](=[O:8])[N:47]([CH2:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:13]([CH2:14][CH3:15])=[N:12]2)=[CH:9][C:10]=1[F:11]

参加物

6

反応物 3

HCID 1001PhenethylamineHCID 7540Triphenyl phosphiteHCID 89841391HCID 89841391、化合物

生成物 1

HCID 89837825HCID 89837825、化合物収率 27.3%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The crude solid (3 g) from step 3 above mixed with triphenyl phosphite (4 mL, 14.81 mmol) in pyridine (15 mL) was stirred at rt for 4 h. The mixture was added with phenethylamine (1.55 mL, 12.18 mmol), irradiated with microwave 250 W to refluxing for 15 min. The mixture was diluted with ethyl acetate (50 mL), washed with water (2×50 mL). The ethyl acetated solution was mixed with water (50 mL) and kept at rt to give solid form. The solution was filtered to give yellow solid title compound (1.1 g, 27.2%). mp=150-152° C. (recrystallized from ethyl acetate); 1H NMR (400 MHz, DMSO-d6) δ 1.19 (t, J=7.2 Hz, 3H, CH3), 2.76 (q, J=7.2 Hz, 2H, CH2), 2.93 (br t, J=7.6 Hz, 2H, CH2), 4.19 (br t, J=7.6 Hz, 2H, CH2), 7.20-7.31 (m, 5H, ArH), 7.80 (d, J=6.4 Hz, 1H, ArH), 7.91 (d, J=8.8 Hz, 1H, ArH); 13C NMR (100 MHz, DMSO-d6) δ 10.6, 26.9, 33.5, 44.8, 112.2, 112.4, 119.8, 119.9, 126.6, 126.8, 127.0, 128.5, 128.7, 128.8, 138.0, 144.1, 153.6, 156.1, 158.9, 160.0; Anal. (C18H16ClFN2O) C, H, N. Calcd: 65.36, 4.88, 8.47. Found: 65.09, 4.77, 8.50.

後処理

  1. customirradiated with microwave 250 W
  2. temperatureto refluxing for 15 min
  3. washwashed with water (2×50 mL)
  4. additionThe ethyl acetated solution was mixed with water (50 mL)
  5. customkept at rt
  6. customto give solid form
  7. filtrationThe solution was filtered

出典と根拠

ORDレコード
ord-1f182c88864e4e1cbb80856e5016f0b3
出典データセット
uspto-grants-2015_10
特許番号
US09155739B2

反応ノート

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