Potassium Carbonate → tert-butyl 4-(1-(cyanomethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate

HRID 1509311ノート

反応式

HRID 1509311 の反応式
[O:1]=[C:2]1[CH2:7][O:6][C:5]2[N:8]=[C:9]([C:18]3[CH:32]=[CH:31][C:21]([CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:20][CH:19]=3)[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:11][C:4]=2[NH:3]1.Br[CH2:34][C:35]#[N:36].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[C:35]([CH2:34][N:3]1[C:2](=[O:1])[CH2:7][O:6][C:5]2[N:8]=[C:9]([C:18]3[CH:19]=[CH:20][C:21]([CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[CH:31][CH:32]=3)[C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:11][C:4]1=2)#[N:36]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 67255587tert-butyl 4-(2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate

生成物 1

HCID 86683672tert-butyl 4-(1-(cyanomethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate収率 15.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

A mixture of tert-butyl 4-(2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)benzylcarbamate (70 mg, 0.162 mmol), 2-bromoacetonitrile (58.4 mg, 0.487 mmol) and potassium carbonate (67.3 mg, 0.487 mmol) in DMF (2 ml) was stirred at 40° C. for 16 h. The reaction mixture was cooled and diluted with water (10 ml) and extracted with DCM (8 mlX3). The combined organic phase was concentrated and the residue was purified by column (biotage, 10 g) eluted with Ethyl acetate/cyclohexane 0-30% to give product 12 mg. 1H NMR (500 MHz, CDCl3) 7.29 (s, 1H), 7.19-7.26 (m, 5H), 7.13 (m, 2H), 7.05 (d, 2H), 4.88 (s, 2H), 4.81 (s, 2H), 4.73 (br, 1H), 4.21 (d, 2H), 1.38 (br, 9H). LCMS (Method D): RT=1.35 min, M+H+=472.2.

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with DCM (8 mlX3)
  3. concentrationThe combined organic phase was concentrated
  4. customthe residue was purified by column (biotage, 10 g)
  5. washeluted with Ethyl acetate/cyclohexane 0-30%

出典と根拠

ORDレコード
ord-8a3951c6779041729aa8d8ec349abb43
出典データセット
uspto-grants-2015_12
特許番号
US09221838B2

反応ノート

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