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 924646ノート

反応式

HRID 924646 の反応式
[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

参加物

6

反応物 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 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-344efb13d3ef42ff9e23098e0493c8e7
出典データセット
uspto-grants-2016_03
特許番号
US09283213B2

反応ノート

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