Acetonitrile → HCID 6480511, compound

HRID 899495Notes

Reaction equation

HRID 899495 reaction equation
Br[CH2:2][CH2:3][OH:4].C([N:7]([CH2:10][CH3:11])[CH2:8][CH3:9])C.[OH:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]2[N:26](CC3C(O)=CC=C(C)N=3)[C:25]3[CH:36]=[C:37]([CH3:41])[CH:38]=[C:39]([CH3:40])[C:24]=3[N:23]=2)[CH2:17][CH2:16]1.[C:42](#N)C>>[OH:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][CH:18]([NH:21][C:22]2[N:23]([CH2:11][C:10]3[C:3]([OH:4])=[CH:2][CH:42]=[C:8]([CH3:9])[N:7]=3)[C:24]3[C:39]([CH3:40])=[CH:38][C:37]([CH3:41])=[CH:36][C:25]=3[N:26]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 108982-BromoethanolHCID 6481585HCID 6481585, compound

Product 1

HCID 6480511HCID 6480511, compoundYield 6.6%

Conditions

Temperature
30 °C

Procedure

A mixture of a-8 (0.0002 mol), a-9 (0.0002 mol), 2-bromo-ethanol (0.0006 mol) and triethylamine (0.0011 mol) in acetonitrile (10 ml) was stirred at 30° C. for 12 hours. The solvent was evaporated until dryness. The residue was taken up in CH2Cl2. The organic layer was washed with H2O, dried (over MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 85/15/1; 10 μm). Two fractions were collected and the solvent was evaporated, yielding: 0.028 g fraction 1 (12.4%) and 0.05 g fraction 2 (22%). Fraction 1 was crystallized from 2-propanone/diisopropylether. The precipitate was filtered off and dried, yielding 0.015 g of 2-{2-[1-(2-hydroxy-ethyl)-piperidin-4-ylamino]-5,7-dimethyl-benzoimidazol-1-ylmethyl}-6-methyl-pyridin-3-ol (6.6%, melting point: 143° C.). Fraction 2 was crystallized from 2-propanone/diisopropylether. The precipitate was filtered off and dried, yielding 0.03 g of 2-{2-[1-(2-hydroxy-ethyl)-piperidin-4-ylamino]-4,6-dimethyl-benzoimidazol-1-ylmethyl}-6-methyl-pyridin-3-ol (compound 2, 13%, melting point: 177° C.).

Workup

  1. customThe solvent was evaporated until dryness
  2. washThe organic layer was washed with H2O
  3. dry with materialdried (over MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 85/15/1; 10 μm)
  7. customTwo fractions were collected
  8. customthe solvent was evaporated
  9. customyielding
  10. customFraction 1 was crystallized from 2-propanone/diisopropylether
  11. filtrationThe precipitate was filtered off
  12. customdried

Sources & evidence

ORD record
ord-90ad77be06bd4abe986975e88072be99
Source dataset
uspto-grants-2008_04
Patent number
US07355051B2

Reaction notes

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