2,2-Dimethyl-1,3-dioxane-4,6-dione → 4-(4-(2H-tetrazol-5-yl)phenyl)-6-(1-methyl-1H-pyrazol-4-yl)-5-phenyl-3,4-dihydropyridin-2(1H)-one

HRID 924646Notes

Reaction equation

HRID 924646 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:4]=[N:3]1.[N:16]1[NH:17][N:18]=[N:19][C:20]=1[C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1.[CH3:29][C:30]1(C)[O:37]C(=O)CC(=O)O1.C([O-])(C)=O.[NH4+:43]>CC(O)=O>[N:16]1[NH:17][N:18]=[N:19][C:20]=1[C:21]1[CH:28]=[CH:27][C:24]([CH:25]2[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[NH:43][C:30](=[O:37])[CH2:29]2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 517165Ammonium AcetateHCID 27606064-(1H-1,2,3,4-tetrazol-5-yl)benzaldehydeHCID 155619131-(1-methyl-1H-pyrazol-4-yl)-2-phenylethanone2×

Product 1

HCID 566444924-(4-(2H-tetrazol-5-yl)phenyl)-6-(1-methyl-1H-pyrazol-4-yl)-5-phenyl-3,4-dihydropyridin-2(1H)-oneYield 3.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(1-methyl-1H-pyrazol-4-yl)-2-phenylethanone (Intermediate 4) (400 mg, 2.0 mmol), 4-(2H-tetrazol-5-yl)benzaldehyde (420 mg, 2.4 mmol), meldrum's acid (345 mg, 2.4 mmol) and AcONH4 (185 mg, 2.4 mmol) in AcOH (4 mL) was refluxed under N2 overnight. The mixture was concentrated in vacuo and the residue was purified by prep-HPLC (0.1% TFA as additive) to give Compound 8 (25 mg, 3%). 1H NMR (DMSO-d6 400 MHz): δ 9.46 (brs, 1H), 7.98 (d, J=8.0 Hz, 2H), 7.58-7.48 (m, 3H), 7.25-7.16 (m, 3H), 7.15 (d, J=6.4 Hz, 2H), 6.91 (s, 1H), 4.00 (d, J=5.2 Hz, 1H), 3.72 (s, 3H), 3.20 (dd, J=16.0 Hz, 7.6 Hz, 1H), 2.50-2.45 (m, 1H). MS (ESI): m/z 398.0 [M+1]+.

Workup

  1. temperaturewas refluxed under N2 overnight
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by prep-HPLC (0.1% TFA as additive)

Sources & evidence

ORD record
ord-344efb13d3ef42ff9e23098e0493c8e7
Source dataset
uspto-grants-2016_03
Patent number
US09283213B2

Reaction notes

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