HCID 86627960, compound → HCID 67269116, compound

HRID 251735Notes

Reaction equation

HRID 251735 reaction equation
[N:1]([CH:4]([C:17]1[N:21]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=2)=[N:19][CH:18]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1([CH2:15][CH3:16])[O:14][CH2:13][CH2:12][O:11]1)=[N+]=[N-]>CCOC(C)=O.[Pd]>[CH2:15]([C:10]1([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([NH2:1])[C:17]2[N:21]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:27])[CH3:28])[C:20]([C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)=[N:19][CH:18]=2)[O:11][CH2:12][CH2:13][O:14]1)[CH3:16]

Participants

4

Reactant 1

HCID 86627960HCID 86627960, compound

Product 1

HCID 67269116HCID 67269116, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The azide (M5) (1 eq.) was dissolved in EtOAc and stirred in the presence of 10% Pd/C under an H2 atmosphere for 1 hr. The H2 atmosphere removed and N2 introduced. The reaction mixture was filtered and the catalyst washed with MeOH and the filtrates concentrated under reduced pressure. The residue was purified by column chromatography eluting with 70% EtOAc/Petroleum ether to afford the amine.

Workup

  1. customThe H2 atmosphere removed
  2. additionN2 introduced
  3. filtrationThe reaction mixture was filtered
  4. washthe catalyst washed with MeOH
  5. concentrationthe filtrates concentrated under reduced pressure
  6. customThe residue was purified by column chromatography
  7. washeluting with 70% EtOAc/Petroleum ether

Sources & evidence

ORD record
ord-c68a0cb1a6c7419cb0f22338e93fe4c9
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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