Ethanol → HCID 45088832, compound

HRID 1441362Notes

Reaction equation

HRID 1441362 reaction equation
OCC(N1[CH2:10][CH2:9][N:8]([C:11]2[CH:33]=[CH:32][C:14]([NH:15]C3N=C(C4N(C(C)C)C(C)=NC=4)C(Cl)=CN=3)=[CH:13][CH:12]=2)[CH2:7]C1)=O.CC[OH:36]>[Pd]>[NH2:15][C:14]1[CH:32]=[CH:33][C:11]([N:8]2[CH2:7][CH:10]([OH:36])[CH2:9]2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 686886412-{4-[4-(Hydroxyacetyl)piperazin-1-yl]anilino}-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)-5-chloropyrimidine

Product 1

HCID 45088832HCID 45088832, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A stirred solution of 1-(4-nitrophenyl)-azetidin-3-ol (Method 36; 15.15 g, 87 mM) in EtOH (250 ml) was hydrogenated over 10% Pd/C (1.5 g) for 18 hrs at atmospheric pressure. The reaction mixture was filtered and the filtrate was evaporated and triturated with ether giving the title compound as a grey crystalline solid. Much of the product had precipitated from the reaction mixture and been filtered off with catalyst. This was stirred with DMF (100 ml) for 15 mins and the catalyst filtered off. The filtrate was evaporated (Hi-Vac) and triturated with a little EtOH. The second crop of product was filtered off, washed with ether and dried. NMR: 3.35 (m+water, 2H), 3.90 (t, 2H), 4.32 (s, 2H), 4.45 (m, 1H), 5.41 (d, 1H), 6.20 (d, 2H), 6.45 (d, 2H); m/z 165.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. customtriturated with ether giving the title compound as a grey crystalline solid
  4. customMuch of the product had precipitated from the reaction mixture
  5. filtrationbeen filtered off with catalyst
  6. filtrationthe catalyst filtered off
  7. customThe filtrate was evaporated (Hi-Vac)
  8. customtriturated with a little EtOH
  9. filtrationThe second crop of product was filtered off
  10. washwashed with ether
  11. customdried

Sources & evidence

ORD record
ord-98262fb2f1c54f0da8b02dd7a1513fc5
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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