4-Heptanol → HCID 22136311, compound

HRID 2113804Notes

Reaction equation

HRID 2113804 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-hexahydro-pyrazolo[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 stirred under an atmosphere of nitrogen at room temperature for 16 h. The solvent was evaporated and the residue was purified by flash column chromatography on silica gel eluting with 15% ethyl acetate/hexane to afford 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 (MH+)=390.

Workup

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

Sources & evidence

ORD record
ord-7202592f3096484ebcac620bf2c0caf1
Source dataset
uspto-grants-2008_10
Patent number
US07432283B2

Reaction notes

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