Methyl 2-azidoacetate → HCID 118103403, compound

HRID 2207430Notes

Reaction equation

HRID 2207430 reaction equation
[N:1]([CH2:4][C:5]([O:7][CH3:8])=[O:6])=[N+:2]=[N-:3].OC(C1C([O-])=C(O)C(=O)O1)CO.[Na+].[C:22]([C:24]1[N:29]=[CH:28][C:27]([C:30]2[CH:31]=[C:32]([NH:37][C:38]3[N:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[CH:40][N:39]=3)[CH:33]=[C:34]([CH3:36])[CH:35]=2)=[CH:26][CH:25]=1)#[CH:23]>C(O)C.O.CN(C=O)C.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:36][C:34]1[CH:35]=[C:30]([C:27]2[CH:26]=[CH:25][C:24]([C:22]3[N:3]=[N:2][N:1]([CH2:4][C:5]([O:7][CH3:8])=[O:6])[CH:23]=3)=[N:29][CH:28]=2)[CH:31]=[C:32]([NH:37][C:38]2[N:43]=[C:42]([C:44]([F:47])([F:45])[F:46])[CH:41]=[CH:40][N:39]=2)[CH:33]=1

Participants

8

Reactant 3

HCID 4020482Methyl 2-azidoacetateHCID 234240007317-67-1HCID 131735920HCID 131735920, compound

Product 1

HCID 118103403HCID 118103403, compound

Reagents, catalysts & solvents 4

HCID 24462Copper SulfateCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl azidoacetate (160 mg, 0.452 mmol), sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate (130 mg, 0.656 mmol), copper sulfate (0.100 mL, 0.100 mmol) in ethanol (2.00 mL) and water (0.500 mL) was added to a solution of N-[3-(6-ethynylpyridin-3-yl)-5-methylphenyl]-4-(trifluoromethyl)pyrimidin-2-amine (100 mg, 0.869 mmol) in DMF (0.500 mL). The mixture was stirred at room temperature for 1 hour. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography (50% ethyl acetate in hexanes) to afford methyl {4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]-1H-1,2,3-triazol-1-yl}acetate. MS APCI C22H19F3N7O2 [M+H]+ 470. found 470. 1H NMR (500 MHz, DMSO-d6) δ 10.29 (s, 1H), 8.89-8.86 (m, 1H), 8.84 (d, J=5.1 Hz, 1H), 8.66 (s, 2H), 8.05-7.98 (m, 1H), 7.58 (s, 1H), 7.28 (d, J=5.1 Hz, 1H), 7.26 (s, 1H), 5.50 (s, 2H), 3.72 (d, J=14.9 Hz, 3H), 2.37 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-acb0c6444a1548cfa647473113d9aa3b
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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