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4-Chlorobenzaldehyde → 4-acetyl-5-(4-chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one

HRID 873952
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HRID 873952 반응식
[CH3:1][C:2]1[N:6]2[CH:7]=[C:8]([NH2:12])[CH:9]=[C:10]([CH3:11])[C:5]2=[N:4][N:3]=1.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.[O:22]=[C:23]([CH2:29][C:30](=[O:32])[CH3:31])[C:24](OCC)=[O:25]>C(O)(=O)C>[C:30]([C:29]1[CH:18]([C:17]2[CH:20]=[CH:21][C:14]([Cl:13])=[CH:15][CH:16]=2)[N:12]([C:8]2[CH:9]=[C:10]([CH3:11])[C:5]3[N:6]([C:2]([CH3:1])=[N:3][N:4]=3)[CH:7]=2)[C:24](=[O:25])[C:23]=1[OH:22])(=[O:32])[CH3:31]
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참가 물질

5

반응물 3

HCID 77264-ChlorobenzaldehydeHCID 69208Ethyl 2,4-dioxovalerateHCID 753574493,8-Dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-amine

생성물 1

HCID 1177026714-acetyl-5-(4-chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one수율 79%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

A mixture of 3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-amine (Step 67.4) (2 g, 12.33 mmol), 4-chlorobenzaldehyde (1.576 g, 11.21 mmol) and ethyl 2,4-dioxopentanoate (1.773 g, 11.21 mmol) in acetic acid (10 mL) was stirred for 2 hr at 100° C. The reaction mixture was concentrated, diluted with CH2Cl2/1N NaOH and extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, evaporated and discarded as they contained no desired product. The aqueous was acidified to pH 3 with 6N HCl and extracted with CH2Cl2. The combined organic extracts were dried over Na2SO4 and concentrated to afford the title compound (3.88 g, 8.80 mmol, 79% yield) as a beige foam. tR: 0.70 min (LC-MS 2); ESI-MS: 397 [M+H]+ (LC-MS 2); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.36 (s, 3H) 2.44 (s, 3H) 2.63 (s, 3H) 6.14 (s, 1H) 7.27 (d, J=8.44 Hz, 2H) 7.33-7.40 (m, 3H) 8.53 (s, 1H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with CH2Cl2/1N NaOH
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customevaporated
  6. extractionextracted with CH2Cl2
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9d6c9abe45054eff8b53b91cf599c4fd
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08975417B2

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