Water → HCID 86758051, compound

HRID 1934588Notes

Reaction equation

HRID 1934588 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:49][N:50]2[CH:54]=[N:53][CH:52]=[N:51]2)[O:13][CH:12]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][C:31]([N:34]5[CH:38]=[N:37][N:36]([CH:39]([CH3:47])[CH:40](OS(C)(=O)=O)[CH3:41])[C:35]5=[O:48])=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH2:11][O:10]1.[N-:55]=[N+:56]=[N-:57].[Na+].O>CN(C=O)C>[N:55]([CH:40]([CH3:41])[CH:39]([N:36]1[C:35](=[O:48])[N:34]([C:31]2[CH:32]=[CH:33][C:28]([N:25]3[CH2:24][CH2:23][N:22]([C:19]4[CH:20]=[CH:21][C:16]([O:15][CH2:14][CH:12]5[CH2:11][O:10][C:9]([C:3]6[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=6[F:1])([CH2:49][N:50]6[CH:54]=[N:53][CH:52]=[N:51]6)[O:13]5)=[CH:17][CH:18]=4)[CH2:27][CH2:26]3)=[CH:29][CH:30]=2)[CH:38]=[N:37]1)[CH3:47])=[N+:56]=[N-:57]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86758052HCID 86758052, compound

Product 1

HCID 86758051HCID 86758051, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of [2S-[2α,4α(S*,S*)]]-4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-[1-methyl-2-[(methylsulfonyl)oxy]propyl]-3H-1,2,4-triazol-3-one (0.0039 mol) and NaN3 (0.005 mol) in DMF (50 ml) was stirred at 85° C. for 48 hours, poured out into H2O and stirred for 30 minutes. The precipitate was filtered off and dissolved in CH2Cl2. The organic solution was washed, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2). The pure fractions were collected and the solvent was evaporated. The residue was triturated in DIPE and 2-propanol, filtered off and dried, yielding 1.1 g (41%) of [2S-[2α,4α(R*,S*)]]-2-(2-azido-1-methylpropyl)-4-[4-[4-[4-[[2-(2,4difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]-phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one; (compound 19).

Workup

  1. stirringstirred for 30 minutes
  2. filtrationThe precipitate was filtered off
  3. dissolutiondissolved in CH2Cl2
  4. washThe organic solution was washed
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. customThe residue was triturated in DIPE and 2-propanol
  12. filtrationfiltered off
  13. customdried

Sources & evidence

ORD record
ord-a84c1589a3594f09969b22ee99a1a501
Source dataset
uspto-grants-2002_05
Patent number
US06384030B1

Reaction notes

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