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 386144Notes

Reaction equation

HRID 386144 reaction equation
[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

Participants

6

Reactant 3

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

Product 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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-6bf400ae7021417bbf58c81af268be9e
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

Loading…