HCID 22466429, compound → HCID 86758053, compound

HRID 1934589Notes

Reaction equation

HRID 1934589 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:58][N:59]2[CH:63]=[N:62][CH:61]=[N:60]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]([CH3:56])[CH:40]([NH:42][CH:43]6[CH2:48][CH2:47][N:46](CC7C=CC=CC=7)[CH2:45][CH2:44]6)[CH3:41])[C:35]5=[O:57])=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH2:11][O:10]1>CO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:58][N:59]2[CH:63]=[N:62][CH:61]=[N:60]2)[O:13][CH:12]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:23][CH2:24][N:25]([C:28]4[CH:33]=[CH:32][C:31]([N:34]5[CH:38]=[N:37][N:36]([CH:39]([CH3:56])[CH:40]([NH:42][CH:43]6[CH2:44][CH2:45][NH:46][CH2:47][CH2:48]6)[CH3:41])[C:35]5=[O:57])=[CH:30][CH:29]=4)[CH2:26][CH2:27]3)=[CH:18][CH:17]=2)[CH2:11][O:10]1.[CH:12]([O:13][CH:9]([CH3:58])[CH3:3])([CH3:14])[CH3:11]

Participants

4

Reactant 1

HCID 22466429HCID 22466429, compound

Product 1

HCID 86758053HCID 86758053, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of [2S-[2α,4α(R*,S*)]]+[2S-[2α,4α(S*,R*)]]-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-[2-[[1-(phenylmethyl)-4-piperidinyl]amino]-1-methylpropyl]-3H-1,2,4-triazol-3-one (0.0046 mol) in methanol (100 ml) was hydrogenated at room temperature for 72 hours with Pd on activated carbon 10% (2 g) as a catalyst. After uptake of H2, the catalyst was filtered off and the filtrate was evaporated. The residue was purified over silica gel on a glass filter (eluent: CH2Cl2/(CH3OH/NH3) 95/5 to 90/10). The pure fractions were collected and the solvent was evaporated. The residue was triturated in DIPE, filtered off and dried, yielding 3 g (84%) of [2S-[2α,4α(R*,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-[2-(4-piperidinylamino)-1-methylpropyl]-3H-1,2,4-triazol-3-one diisopropylether(1:1) (compound 63).

Workup

  1. filtrationAfter uptake of H2, the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified over silica gel on a glass
  4. filtrationfilter (eluent: CH2Cl2/(CH3OH/NH3) 95/5 to 90/10)
  5. customThe pure fractions were collected
  6. customthe solvent was evaporated
  7. customThe residue was triturated in DIPE
  8. filtrationfiltered off
  9. customdried

Sources & evidence

ORD record
ord-ce407b18aa61410a8fd60da3c46a4046
Source dataset
uspto-grants-2002_05
Patent number
US06384030B1

Reaction notes

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