2-Pyridinecarboxaldehyde → HCID 11243888, compound

HRID 459923Notes

Reaction equation

HRID 459923 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=2)[CH2:3][CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH:37]=O>C(Cl)Cl>[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH2:37][N:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 18445311HCID 18445311, compound

Product 1

HCID 11243888HCID 11243888, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine 6-(piperidin-4-yloxy)-nicotinamide (100 mg, 0.45 mmol) with sodium triacetoxy-borohydride (124 mg, 0.59 mmol) and pyridine-2-carbaldehyde (43 μL, 045 mmol) in CH2Cl2 (1.5 mL). Stir the reaction mixture for 3 h. Then, dilute the reaction mixture with CH2Cl2 (5 mL) and washed with NaOH (1M aq, 5 mL). Dry the organic layer over sodium sulfate, filter and concentrate. Purify the residue through an SCX chromatography to provide the title compound (83 mg, 59%). Mass spectrum (ion spray): m/z=313.1 (M+1); 1H NMR (DMSO-d6): 8.67 (ad, J=2.2 Hz, 1H), 8.50 (m, 1H), 8.12 (dd, J=2.6 and 8.8 Hz, 1H), 7.98 (bs, 1H), 7.80–7.76 (m, 1H), 7.47 (d, J=7.9 Hz, 1H), 7.41 (bs, 1H), 7.29–7.26 (m, 1H), 6.84 (d, J=8.8 Hz, 1H), 5.10 (m, 1H), 3.63 (m, 2H), 2.77–2.74 (m, 2H), 2.35–2.30 (m, 2H), 1.99 (bs, 2H), 1.75–1.69 (m, 2H).

Workup

  1. washwashed with NaOH (1M aq, 5 mL)
  2. dry with materialDry the organic layer over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the residue through an SCX chromatography

Sources & evidence

ORD record
ord-5e4d29c94dcf4e60a32534f3972b77b2
Source dataset
uspto-grants-2007_03
Patent number
US07196100B2

Reaction notes

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