Trimethylsilylmethyl Azide → 2-{[6-(Morpholin-4-ylmethyl)pyridin-2-yl]amino}-5-{1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}thiophene-3-carboxamide

HRID 386144

反応式

HRID 386144 の反応式
[C:1]([C:3]1[S:7][C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[N:10]=2)=[C:5]([C:22]([NH2:24])=[O:23])[CH:4]=1)#[CH:2].[CH3:25][Si:26]([CH2:29][N:30]=[N+:31]=[N-:32])([CH3:28])[CH3:27].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CN(C=O)C.O>[N:16]1([CH2:15][C:11]2[N:10]=[C:9]([NH:8][C:6]3[S:7][C:3]([C:1]4[N:32]=[N:31][N:30]([CH2:29][Si:26]([CH3:28])([CH3:27])[CH3:25])[CH:2]=4)=[CH:4][C:5]=3[C:22]([NH2:24])=[O:23])[CH:14]=[CH:13][CH:12]=2)[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1

参加物

6

反応物 3

HCID 150751Trimethylsilylmethyl AzideHCID 23667548Sodium AscorbateHCID 595262705-Ethynyl-2-{[6-(morpholin-4-ylmethyl)pyridin-2-yl]amino}thiophene-3-carboxamide

生成物 1

HCID 595255682-{[6-(Morpholin-4-ylmethyl)pyridin-2-yl]amino}-5-{1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}thiophene-3-carboxamide

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

5-Ethynyl-2-{[6-(morpholin-4-ylmethyl)pyridin-2-yl]amino}thiophene-3-carboxamide (Example 599, Step 4) (75 mg, 0.22 mmol) and trimethylsilylmethyl azide (0.65 ml, 0.44 mmol) were combined in DMF (1.0 mL). CuSO4.5H2O (5.5 mg, 0.022 mmol) in water (0.2 mL) and sodium ascorbate (17 mg, 0.088 mmol) in water (0.2 ml) were added, and the reaction mixture was stirred at room temperature overnight. The reaction was evaporated to dryness, combined with MeOH and silica gel, and evaporated. Flash chromatography (dry load, 0-10% MeOH/EtOAc) afforded the title compound a yellow solid.

後処理

  1. customThe reaction was evaporated to dryness
  2. customevaporated
  3. dry with materialFlash chromatography (dry load, 0-10% MeOH/EtOAc)

出典と根拠

ORDレコード
ord-6bf400ae7021417bbf58c81af268be9e
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

関連ノート

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