Acetic Acid → HCID 16737506, compound

HRID 2264546Notes

Reaction equation

HRID 2264546 reaction equation
[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]3[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=3)=[CH:10][C:9]=2[CH:21]=1)[CH:2]([CH3:4])[CH3:3].C(O)(=O)C.[NH:26]1[CH2:31][CH2:30][CH:29]([C:32]([OH:34])=[O:33])[CH2:28][CH2:27]1.C([BH3-])#N.[Na+]>C(Cl)Cl.CO.CS(C)=O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]3[CH:14]=[CH:15][C:16]([CH2:17][N:26]4[CH2:31][CH2:30][CH:29]([C:32]([OH:34])=[O:33])[CH2:28][CH2:27]4)=[CH:19][CH:20]=3)=[CH:10][C:9]=2[CH:21]=1)[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 37734-Piperidinecarboxylic acidHCID 5003444Sodium cyanoborohydrideHCID 59595889HCID 59595889, compound

Product 1

HCID 16737506HCID 16737506, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 4-(5-isobutylbenzofuran-2-yl)benzaldehyde (22 mg, 0.08 mmol), acetic acid (7 μL, 0.12 mmol) and piperidine-4-carboxylic acid (15 mg, 0.12 mmol) in DCM/MeOH (1:1, 1.4 mL) was stirred at room temperature for 1 h. Sodium cyanoborohydride (2.5 mg, 0.04 mmol) was added and the reaction mixture was stirred for 4 h at room temperature. After concentration of solvent under reduced pressure, the resulting residue was dissolved in an aliquot of DMSO and purified by reverse phase preparative HPLC (Phenomenex reverse phase Luna 5μ C18(2) column, 60×21.2 mm ID) to yield the desired final product (1 6.9 mg, 55%): >95% purity by LCMS, ESI-MS: 392.0 (M+H)+, 1H NMR (400 MHz, CD3OD) δ 8.01 (d, 2H), 7.59 (d, 2H), 7.43 (d, 1H), 7.39 (s, 1H), 7.26 (s, 1H), 7.13 (dd, 1H), 4.36 (s, 2H), 3.58(m, 2H), 3.10 (m, 2H), 2.65(m, 1H), 2.57 (d, 2H), 1.90 (m, 1H), 0.92 (d, 6H).

Workup

  1. stirringthe reaction mixture was stirred for 4 h at room temperature
  2. custompurified by reverse phase preparative HPLC (Phenomenex reverse phase Luna 5μ C18(2) column, 60×21.2 mm ID)

Sources & evidence

ORD record
ord-302de4a1b80f43648c8ec5e2e0ceed67
Source dataset
uspto-grants-2010_12
Patent number
US07855193B2

Reaction notes

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