1,2-Dichloroethane → HCID 68275987, compound

HRID 1475949Notes

Reaction equation

HRID 1475949 reaction equation
[CH2:1]([N:6]([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[C:7]([C:9]1[CH:14]=[CH:13][N:12]2[N:15]=[C:16]([C:18](O)=[O:19])[CH:17]=[C:11]2[CH:10]=1)=[O:8])[CH2:2][CH:3]([CH3:5])[CH3:4].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[NH:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([N:6]([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[C:7]([C:9]1[CH:14]=[CH:13][N:12]2[N:15]=[C:16]([C:18]([N:47]3[CH2:52][CH2:51][O:50][CH2:49][CH2:48]3)=[O:19])[CH:17]=[C:11]2[CH:10]=1)=[O:8])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 68275986HCID 68275986, compound

Product 1

HCID 68275987HCID 68275987, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(diisopentylcarbamoyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid (0.29 g, 0.840 mmol), EDC (0.274 g, 1.427 mmol) and HOBT (0.219 g, 1.427 mmol) were combined in DMF (2.0 ml). Added triethylamine (0.351 ml, 2.52 mmol) and morpholine (0.073 ml, 0.840 mmol) and stirred at 22° C. for 12 h. The mixture was diluted with ethyl acetate (25 ml) and washed with water, saturated sodium bicarbonate solution and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography: ISCO Gold 24 g using 0% to 100% ethyl acetate in hexanes over 11 min. Pooled and concentrated desired fractions to afford, 0.26 g (74%) of the title compound as a clear oil. LCMS m/z 415.3 (M+H)+. ret. time=2.27 min.

Workup

  1. washwashed with water, saturated sodium bicarbonate solution and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. customover 11 min
  7. concentrationPooled and concentrated desired fractions
  8. customto afford

Sources & evidence

ORD record
ord-61c0785adb1b4069b260c32c5bc011df
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

Loading…