Hydrochloric Acid → HCID 58495481, compound

HRID 1190972Notes

Reaction equation

HRID 1190972 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:7][CH2:6][CH2:5][CH:4]([O:8][C:9]2[N:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)[CH2:3]1.B.C1COCC1.Cl>C1COCC1>[NH2:16][CH2:15][C:12]1[CH:13]=[N:14][C:9]([O:8][CH:4]2[CH2:5][CH2:6][CH2:7][C:2]([CH3:17])([CH3:1])[CH2:3]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 58495453HCID 58495453, compound

Product 1

HCID 58495481HCID 58495481, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 6-(3,3-dimethyl-cyclohexyloxy)-pyridine-3-carbonitrile (9.14 g, 39.7 mmoles) in THF (20 mL) at 0° C. under nitrogen and add borane-THF complex (119 mL, 119 mmol, 1M solution in THF). Stir the resulting solution overnight while warming to room temperature. Slowly add the reaction mixture to a mixture of 5N aqueous HCl (100 mL) and THF (50 mL) at 0° C. and stir for 2 h. Concentrate in vacuo and take-up the residue in a minimum amount of methanol for filtration through a SCX-2 column (10 g) eluting with methanol followed by 3N ammonia in methanol to obtain the desired intermediate as an oil (5.85 g, 63%). MS (ES+) m/z: 207 (M+H)+.

Workup

  1. additionSlowly add the reaction mixture
  2. stirringstir for 2 h
  3. concentrationConcentrate in vacuo
  4. filtrationfor filtration through a SCX-2 column (10 g)
  5. washeluting with methanol

Sources & evidence

ORD record
ord-21e0c18817744e5f84ca4b01b9ec525d
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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