Tetrahydrofuran → (S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-ol

HRID 388094ノート

反応式

HRID 388094 の反応式
[Br:1][C:2]1[N:7]=[C:6]2[N:8]([C@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH3:13])[C:9](=[O:11])[NH:10][C:5]2=[N:4][CH:3]=1.BrC1N=C(N[C@H:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:29])C(N)=NC=1.[C:37](N1C=CN=C1)([N:39]1C=CN=C1)=O.O1CCC[CH2:50]1>CO>[CH3:50][N:10]1[C:5]2=[N:4][CH:3]=[C:2]([C:35]3[CH:34]=[CH:33][CH:32]=[C:31]4[C:30]=3[CH:28]=[CH:29][CH:37]=[N:39]4)[N:7]=[C:6]2[N:8]([C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[C:9]1=[O:11].[Br:1][C:2]1[N:7]=[C:6]2[N:8]([C@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH3:13])[C:9](=[O:11])[NH:10][C:5]2=[N:4][CH:3]=1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 24815573(S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-olHCID 57880841HCID 57880841、化合物

生成物 2

HCID 24815573(S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-ol収率 62%HCID 66699676(S)-1-Methyl-3-(1-phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

(S)-6-Bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. The title compound was prepared using (S)-6-bromo-N2-(1-phenylethyl)pyrazine-2,3-diamine (See Example 3.A) (0.50 g, 1.71 mmol), 1,1′-carbonyldiimidazole (0.35 g, 2.13 mmol), and tetrahydrofuran (7 mL) as described in General Procedure D1. The crude material was dissolved in methanol (5 mL), and the product was triturated with H2O while sonicating. The resulting precipitate was filtered and dried in a vacuum oven overnight to afford 0.34 g (1.07 mmol, 62%) of (S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. MS (ESI) m/z 319.4 [M+1]+.

後処理

  1. customthe product was triturated with H2O
  2. customwhile sonicating
  3. filtrationThe resulting precipitate was filtered
  4. customdried in a vacuum oven overnight

出典と根拠

ORDレコード
ord-c5b65e77832c40acb870a62bbb8e16f1
出典データセット
uspto-grants-2013_02
特許番号
US08372976B2

反応ノート

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