Cyclohexane → HCID 66576409, compound

HRID 1775598Notes

Reaction equation

HRID 1775598 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]2[N:14]([CH:23]([CH3:29])[C:24](OCC)=[O:25])[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:3]=12.[H-].C([Al+]CC(C)C)C(C)C.C1CCCCC1.[Cl-].[NH4+]>C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:6][N:5]=[C:4]2[N:14]([CH:23]([CH3:29])[CH2:24][OH:25])[N:15]=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:3]=12

Participants

7

Reactant 4

HCID 8078CyclohexaneHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 70982130HCID 70982130, compound

Product 1

HCID 66576409HCID 66576409, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) stirred solution of ethyl 2-(4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)propanoate (72 mg, 0.177 mmol) in THF (0.5 mL) was added dropwise a 1.1 M solution of diisobutylaluminum hydride in cyclohexane (1 mL, 1.1 mmol). After 15 minutes, a saturated solution of ammonium chloride and CH2Cl2 were added at 0° C. to the reaction mixture. The aqueous phase was extracted with CH2Cl2 and the organic phases combined, dried over MgSO4, filtered and evaporated. Purification using preparative HPLC gave Compound 96 as an off-white solid (28 mg).

Workup

  1. extractionThe aqueous phase was extracted with CH2Cl2
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customPurification

Sources & evidence

ORD record
ord-fb47bea2e86243e3bffb1d6aa132c8bf
Source dataset
uspto-grants-2016_02
Patent number
US09260381B2

Reaction notes

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