Potassium Hydroxide → trans-(4,5-Dihydro-5-(2-methoxypyridin-3-yl)oxazol-4-yl)(pyrrolidin-1-yl)methanone

HRID 75716Notes

Reaction equation

HRID 75716 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH:9]=[O:10])=[CH:7][CH:6]=[CH:5][N:4]=1.[OH-].[K+].[N+:13]([CH2:15][C:16]([N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:17])#[C-:14]>CO>[CH3:1][O:2][C:3]1[C:8]([C@@H:9]2[O:10][CH:14]=[N:13][C@H:15]2[C:16]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 6455476Pyrrolidine, 1-(isocyanoacetyl)-HCID 125333912-Methoxypyridine-3-carbaldehyde

Product 1

HCID 66901584trans-(4,5-Dihydro-5-(2-methoxypyridin-3-yl)oxazol-4-yl)(pyrrolidin-1-yl)methanoneYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

BAL 01014 was prepared in accordance with method D using 2-methoxy-3-pyridinecarboxaldehyde (0.64 ml, 5.43 mmol), KOH (0.305 mg, 5.43 mmol) in methanol (5 mL) and 2-isocyano-1-(pyrrolidin-1-yl)ethanone BLE 04098 (0.75 g, 5.43 mmol). After work-up trans-(4,5-dihydro-5-(2-methoxypyridin-3-yl)oxazol-4-yl)(pyrrolidin-1-yl)methanone BAL 01014 was obtained (0.74 mg, 50% yield) as a white solid.

Workup

  1. customBAL 01014 was prepared in accordance with method D

Sources & evidence

ORD record
ord-7eda041cba71432a8c31b17facd210dd
Source dataset
uspto-grants-2014_09
Patent number
US08835463B2

Reaction notes

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