4-Heptanol → HCID 22136311, compound

HRID 916221Notes

Reaction equation

HRID 916221 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2[C:16](=[O:20])[N:17]([CH3:19])[NH:18][C:11]1=2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:40][CH2:41][CH2:42][CH:43](O)[CH2:44][CH2:45][CH3:46].CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2=[C:16]([O:20][CH:43]([CH2:44][CH2:45][CH3:46])[CH2:42][CH2:41][CH3:40])[N:17]([CH3:19])[N:18]=[C:11]12

Participants

6

Reactant 4

HCID 115134-HeptanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 12143941HCID 12143941, compound

Product 1

HCID 22136311HCID 22136311, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 200 mg of 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-1,2,4,5,6,7-hexahydropyrazolo[3,4-b]pyridin-3-one (Example 1, step 5) and 337 mg of triphenylphosphine in 15 mL of dry tetrahydrofuran was treated with 124 mg of 4-heptanol and 224 mg of diethylazodicarboxylate. The mixture was placed under an atmosphere of nitrogen and stirred at room temperature for 16 h. The solvent was evaporated and the residue was purified by flash column chromatography on silica gel using 15% ethyl acetate/hexane as solvent giving 84 mg of 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-3-(1-propylbutoxy)-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridine as a colorless oil, ms m/z 390 (MH+).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash column chromatography on silica gel using 15% ethyl acetate/hexane as solvent

Sources & evidence

ORD record
ord-3d0478e18fa14d9ba48a4ae9f5cbd187
Source dataset
uspto-grants-2007_09
Patent number
US07268146B2

Reaction notes

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