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

반응식

HRID 386144 반응식
[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

참가 물질

6

반응물 3

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

생성물 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

시약·촉매·용매 2

HCID 962Water용매2회HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-6bf400ae7021417bbf58c81af268be9e
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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