Sodium hydride → US9777003, Example 24

HRID 628265ノート

反応式

HRID 628265 の反応式
[H-].[Na+].[CH3:3][C:4]1[N:8]2[C:9]3[CH:15]=[C:14]([CH3:16])[NH:13][C:10]=3[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1.Br[CH:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:19][CH2:20][CH2:21][CH3:22]>CN(C=O)C>[CH3:3][C:4]1[N:8]2[C:9]3[CH:15]=[C:14]([CH3:16])[N:13]([CH:18]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:19][CH2:20][CH2:21][CH3:22])[C:10]=3[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 10900349(1-Bromopentyl)benzeneHCID 1369631111,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine

生成物 1

HCID 118159523US9777003, Example 24

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (0.011 g, 0.27 mmol, 60% in mineral oil) was added to a solution of 1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (50.0 mg, 0.268 mmol, from Example 2, Step 5) in DMF (6 mL). After stirring for 10 minutes, (1-bromopentyl)benzene (0.061 g, 0.27 mmol, from Step 1) was added. After stirring for 45 minutes, the reaction was quenched by the addition of water and the mixture was diluted with MeCN, filtered and purified via preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (0.01 g, 10%).

後処理

  1. stirringAfter stirring for 45 minutes
  2. customthe reaction was quenched by the addition of water
  3. additionthe mixture was diluted with MeCN
  4. filtrationfiltered
  5. custompurified via preparative HPLC-MS (Waters XBridge C18
  6. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (0.01 g, 10%)

出典と根拠

ORDレコード
ord-d5663a6d55b741bd9316bd34c98067b8
出典データセット
uspto-grants-2016_04
特許番号
US09309246B2

反応ノート

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