HCID 6481592, compound → HCID 67053684, compound

HRID 899497Notes

Reaction equation

HRID 899497 reaction equation
C(O[C:4](=[O:34])[CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]2[N:18]([CH2:19][C:20]3[C:25]([OH:26])=[CH:24][CH:23]=[C:22]([CH3:27])[N:21]=3)[C:17]3[CH:28]=[C:29]([CH3:33])[CH:30]=[C:31]([CH3:32])[C:16]=3[N:15]=2)[CH2:9][CH2:8]1)C.CO.[NH3:37]>>[OH:26][C:25]1[C:20]([CH2:19][N:18]2[C:17]3[CH:28]=[C:29]([CH3:33])[CH:30]=[C:31]([CH3:32])[C:16]=3[N:15]=[C:14]2[NH:13][CH:10]2[CH2:9][CH2:8][N:7]([CH2:6][CH2:5][C:4]([NH2:37])=[O:34])[CH2:12][CH2:11]2)=[N:21][C:22]([CH3:27])=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 6481592HCID 6481592, compoundHCID 21705897Ammonia methanol

Product 1

HCID 67053684HCID 67053684, compoundYield 30%

Conditions

Temperature
70 °C

Procedure

A mixture of 3-{4-[1-(3-Hydroxy-6-methyl-pyridin-2-ylmethyl)-4,6-dimethyl-1H-benzoimidazol-2-ylamino]-piperidin-1-yl}-propionic acid ethyl ester (0.0065 mol) in methanol/NH3 7N (15 ml) was stirred in a sealed vessel at 70° C. for 12 hours. The solvent was evaporated until dryness. The residue (0.3 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 85/14/1; 5 μm). The pure fractions were collected and the solvent was evaporated. The residue (0.09 g, 32%) was crystallized from diisopropylether. The precipitate was filtered off and dried, yielding 0.086 g of 3-{4-[1-(3-hydroxy-6-methyl-pyridin-2-ylmethyl)-4,6-dimethyl-1H-benzoimidazol-2-ylamino]-piperidin-1-yl}-propionamide (compound 5, 30%, melting point: 212° C.).

Workup

  1. customThe solvent was evaporated until dryness
  2. customThe residue (0.3 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 85/14/1; 5 μm)
  3. customThe pure fractions were collected
  4. customthe solvent was evaporated
  5. customThe residue (0.09 g, 32%) was crystallized from diisopropylether
  6. filtrationThe precipitate was filtered off
  7. customdried

Sources & evidence

ORD record
ord-c6ed8a493363455fb529b56d3e655cc1
Source dataset
uspto-grants-2008_04
Patent number
US07355051B2

Reaction notes

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