3-Pyridinecarboxaldehyde → HCID 22618246, compound

HRID 842111Notes

Reaction equation

HRID 842111 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:10][C:11]2[O:12][C:13]3[C:19]([NH2:20])=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]=O)[CH:27]=1.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.Cl>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:10][C:11]2[O:12][C:13]3[C:19]([NH:20][CH2:32][C:28]4[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=4)=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 103713-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 9880976HCID 9880976, compound

Product 1

HCID 22618246HCID 22618246, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolvent3×

Procedure

To a stirred suspension of 2-(3-cyclopentyloxy-4-methoxybenzyl)-7-aminobenzoxazole (0.98 g, 0.0029 mol) in 15 ml of methanol, 2.5 ml of 1 N HCl in methanol, was added. Pyridine-3-carboxaldehyde (0.37 g, 3.5 mmol) was added to this suspension followed by sodium cyanoborohydride (0.29 g, 0.0046 mol) and the pH was adjusted to 6 using 1 N HCl in methanol. After 3 hours, 1 N sodium hydroxide was added to bring the pH to 10 and the reaction mixture was extracted with CH2Cl2. The CH2Cl2 layer was separated and the aqueous layer was extracted with 2×50 ml of CH2Cl2. The combined CH2Cl2 layers were washed with water, dried and evaporated to give 1.09 g of yellow oil which crystallized on trituration with ether. After filtration, 0.5 g of white crystalline title compound was separated and the filtrate was concentrated. Flash chromatography of the filtrate on silica gel gave 0.2 g of recovered starting material on elution with CH2Cl2, followed by a further 0.32 g of crystalline title compound when the eluting solvent was 1% methanol in CH2Cl2. This material could be recrystallized from an ether-hexane blend to give the title compound as off-white crystals, mp 90-92° C.

Workup

  1. additionwas added
  2. extractionthe reaction mixture was extracted with CH2Cl2
  3. customThe CH2Cl2 layer was separated
  4. extractionthe aqueous layer was extracted with 2×50 ml of CH2Cl2
  5. washThe combined CH2Cl2 layers were washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-ee693e974a334ccf96e6039c9e732191
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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