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 924646노트

반응식

HRID 924646 반응식
[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

참가 물질

6

반응물 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-phenylethanone2회

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-344efb13d3ef42ff9e23098e0493c8e7
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09283213B2

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