Acetic Acid → HCID 16737506, compound

HRID 2075142Notes

Reaction equation

HRID 2075142 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 (16.9 mg, 55%) [hS1P1 EC50=1700 nM, >25000]: >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-68d1e98bcd6f45b3b1ef75d4b3d12933
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

Loading…