3-Pyridinecarboxaldehyde → HCID 44467383, compound

HRID 1642435Notes

Reaction equation

HRID 1642435 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[S:21][CH:20]=[CH:19][N:5]2[C:6](=[O:18])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]=O)[CH:23]=1.[O-]CC.[Na+]>C(O)C>[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](/[CH:28]=[CH:1]/[C:2]2[N:3]=[C:4]3[S:21][CH:20]=[CH:19][N:5]3[C:6](=[O:18])[C:7]=2[C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:10][CH:9]=2)[CH:23]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 2723922Sodium ethoxideHCID 667528027-Methyl-6-[4-(trifluoromethyl)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 44467383HCID 44467383, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was synthesized by condensation of Intermediate 5 (400 mg, 1.289 mmol) with pyridine-3-carbaldehyde (200 mg, 1.867 mmol) in presence of sodium ethoxide (175 mg, 2.578 mmol) in ethanol (20 ml) according to the procedure described in Example 24 to give 267 mg of the desired product as a pale yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 6.91 (d, J=15.6 Hz, 1H), 7.31-7.38 (m, 1H), 7.55-7.61 (m, 3H), 7.80-7.88 (m, 4H), 8.00-8.06 (m, 1H), 8.41-8.49 (m, 1H), 8.65-8.72 (m, 1H); ESI-MS (m/z) 400.25 (M+H)+.

Sources & evidence

ORD record
ord-f38a3bc2725b43a3979b8476b7fb5ff2
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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