3-Pyridinecarboxaldehyde → HCID 68959247, compound

HRID 1423894Notes

Reaction equation

HRID 1423894 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.[OH-].[K+].[N+:11]([CH2:13][C:14]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[O:15])#[C-:12]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]2[O:8][CH:12]=[N:11][C@H:13]2[C:14]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)=[O:15])[CH:2]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 14797Potassium HydroxideHCID 6455475Morpholine, 4-(isocyanoacetyl)-2×

Product 1

HCID 68959247HCID 68959247, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

SLA 09050A was prepared in accordance with method D using pyridine-3-carbaldehyde (0.65 mL, 4.86 mmol), KOH (0.273 mg, 4.86 mmol) in methanol (10 mL) and 2-isocyano-1-morpholinoethanone SLA 07118 (0.75 g, 4.86 mmol). The solution was stirred for 20 h at 0° C. After work-up (without any further purification), evaporation and drying trans-(4,5-dihydro-5-(pyridin-3-yl)oxazol-4-yl)(morpholino)methanone SLA 09050A was obtained as a yellow solid (0.92 g, 72.5% yield).

Workup

  1. customAfter work-up (without any further purification),
  2. customevaporation
  3. dry with materialdrying trans-(4,5-dihydro-5-(pyridin-3-yl)oxazol-4-yl)(morpholino)methanone SLA 09050A

Sources & evidence

ORD record
ord-34d8a711dd5f43bda8b71f084bed415e
Source dataset
uspto-grants-2015_01
Patent number
US08927589B2

Reaction notes

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