Triethylamine → HCID 178426677, compound

HRID 2037322Notes

Reaction equation

HRID 2037322 reaction equation
[CH2:1]([C:5]1[C:6]([CH3:13])=[CH:7][C:8]([C:11]#[N:12])=[N:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3].C(N(CC)CC)C.Cl.[NH2:22][OH:23]>CO>[OH:23][NH:22][C:11]([C:8]1[CH:7]=[C:6]([CH3:13])[C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:10][N:9]=1)=[NH:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 686283435-Isobutyl-4-methyl-pyridine-2-carbonitrile

Product 1

HCID 178426677HCID 178426677, compoundYield 123%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 5-isobutyl-4-methyl-pyridine-2-carbonitrile (106 mg, 608 μmol) in methanol (3 mL), triethylamine (123 mg, 1.22 mmol) and hydroxylamine hydrochloride (63 mg, 913 μmol) is added. The mixture is stirred at 75° C. for 18 h before it is concentrated. The residue is dissolved in aq. NaHCO3 (pH 7-8) and extracted with DCM (6×50 mL). The org. extracts are combined, dried over MgSO4, filtered, concentrated and dried to give the title compound (155 mg) as a white solid; LC-MS: tR=0.67 min, [M+1]+=208.01; 1H NMR (CD3OD): δ0.97 (d, J=6.8 Hz, 6H), 1.84-1.96 (m, 1H), 2.37 (s, 3H), 2.58 (d, J=7.3 Hz, 2H), 7.67 (s, 1H), 8.26 (s, 1H).

Workup

  1. concentrationis concentrated
  2. dissolutionThe residue is dissolved in aq. NaHCO3 (pH 7-8)
  3. extractionextracted with DCM (6×50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried

Sources & evidence

ORD record
ord-6c53aefacff8406080cc3eea8458ab2e
Source dataset
uspto-grants-2013_11
Patent number
US08575200B2

Reaction notes

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