Acetic Acid → HCID 68467882, compound

HRID 2060869Notes

Reaction equation

HRID 2060869 reaction equation
[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=2)=[CH:5][CH:4]=1)=O.C(O)(=O)C.[CH3:26][CH:27]([CH3:31])[CH2:28][CH2:29][NH2:30].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[ClH:46].O1CCOCC1>C(Cl)Cl.CCOCC>[ClH:46].[CH3:26][CH:27]([CH3:31])[CH2:28][CH2:29][NH:30][CH2:1][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=2)=[CH:5][CH:4]=1

Participants

9

Reactant 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 7894IsoamylamineHCID 312751,4-DioxaneHCID 5049666Sodium triacetoxyborohydrideHCID 59401379HCID 59401379, compound

Product 1

HCID 68467882HCID 68467882, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-(4-formylnaphthalen-1-yloxy)nicotinonitrile (Preparation 1) (1.50 g, 5.47 mmol) in DCM (15 mL) was added acetic acid (0.98 mL, 16.42 mmol) and 3-methylbutylamine (1.91 mL, 16.42 mmol). After 1 h NaBH(OAc)3 (3.48 g, 16.42 mmol) and DCM (20 mL) were added. The reaction was stirred at rt for a further 16 h. The mixture was partitioned between DCM (150 mL) and saturated NaHCO3 (200 mL), the organic phase washed with water (200 mL) and dried (MgSO4). Solvent removed in vacuo. To the residue was added ether (10 mL) followed by 4M HCl in dioxane (1.0 mL, 4.0 mmol). A further 40 mL of ether was added and the resulting precipitate filtered and dried under vacuum to give the title compound: RT=2.84 min; m/z (ES+)=346.2 [M+H]+.

Workup

  1. customThe mixture was partitioned between DCM (150 mL) and saturated NaHCO3 (200 mL)
  2. washthe organic phase washed with water (200 mL)
  3. dry with materialdried (MgSO4)
  4. customSolvent removed in vacuo
  5. additionTo the residue was added ether (10 mL)
  6. filtrationthe resulting precipitate filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-d96f1e49fa994835a4c79568fa267ae3
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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