Phenylacetyl chloride → 5-(4-Acetoxyphenyl)-3-benzyl-2-(phenylacetylamino)pyrazine

HRID 1970790ノート

反応式

HRID 1970790 の反応式
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:14]([NH2:17])=[N:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:25]1([CH2:31][C:32](Cl)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:12]=[C:13]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:14]([NH:17][C:32](=[O:33])[CH2:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:15][CH:16]=2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

参加物

6

反応物 3

HCID 7679Phenylacetyl chlorideHCID 516892Sodium BicarbonateHCID 670035525-(4-Acetoxyphenyl)-2-amino-3-benzylpyrazine

生成物 1

HCID 670032925-(4-Acetoxyphenyl)-3-benzyl-2-(phenylacetylamino)pyrazine収率 20.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

Under an argon atmosphere, 5-(4-acetoxyphenyl)-2-amino-3-benzylpyrazine (c-19) (194 mg, 607 μmol) was dissolved in pyridine (2 mL) and to this was added 4-(dimethylamino)pyridine (7.8 mg, 64 μmol) and cooled to 0° C. To this was added phenylacetyl chloride (160 μL, 1.21 mmol) and stirred for 2 h after warming to room temperature. To this was added saturated aqueous solution of sodium bicarbonate to stop the reaction and after collecting the precipitate by filtration using a Kiriyama funnel, the residue was dried in vacuo to give 5-(4-acetoxyphenyl)-3-benzyl-2-(phenylacetylamino)pyrazine (c-30) as a colorless solid (53.9 mg, 20.3%). Rf=0.24 (n-hexane/ethyl acetate=3/2). Mp. 228-231° C. UV (MeOH, 0.3% DMSO) λmax (log ε) 318 (4.19), 290 (4.17), 259 (4.24). 1H NMR (400 MHz, DMSO-d6) δ 2.29 (s, 3H), 3.68 (s, 2H), 4.07 (s, 2H), 7.01-7.08 (AA′BB′, 2H), 7.11-7.22 (m, 3H), 7.23-7.29 (m, 3H), 7.31-7.38 (m, 4H), 8.07-8.14 (AA′BB′, 2H), 8.93 (s, 1H), 10.57 (s, 1H). IR (KBr, cm−1) 706, 851, 918, 1157, 1206, 1223, 1346, 1366, 1410, 1449, 1495, 1543, 1576, 1670, 1755, 3248. HRMS (FAB+) m/z 438.1806 (M+H, C27H24N3O3 requires 438.1818).

後処理

  1. temperatureafter warming to room temperature
  2. customthe reaction
  3. customafter collecting the precipitate
  4. filtrationby filtration
  5. customthe residue was dried in vacuo

出典と根拠

ORDレコード
ord-efb103485de240f2a87b3205377bc529
出典データセット
uspto-grants-2013_04
特許番号
US08431525B2

反応ノート

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