Hydrochloric Acid → 4-[3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridin-2-yl]benzaldehyde

HRID 1920033

반응식

HRID 1920033 반응식
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[N:17][C:18]=3[C:28]3[CH:29]=[N:30][NH:31][CH:32]=3)[N:13]=2)=[CH:8][CH:7]=1.Cl>CN1C(=O)CCC1>[C:22]1([C:21]2[C:12]([C:9]3[CH:8]=[CH:7][C:6]([CH:2]=[O:1])=[CH:11][CH:10]=3)=[N:13][C:14]3[C:19]([CH:20]=2)=[C:18]([C:28]2[CH:29]=[N:30][NH:31][CH:32]=2)[N:17]=[CH:16][CH:15]=3)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 57500724HCID 57500724, 화합물

생성물 1

HCID 575007264-[3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridin-2-yl]benzaldehyde

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
80 °C

실험 절차

To a solution of 2-[4-(1,3-dioxolan-2-yl)phenyl]-3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridine (1-2) (1.0 g, 2.4 mmol) in NMP (25 mL) was added 6N HCl (10 mL). The reaction was heated at 80° C. for 1 hour. The reaction mixture was cooled to room temperature, slowly quenched into saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated under vacuum to give 4-[3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridin-2-yl]benzaldehyde (1-3) as a white solid. MS (M+H)+: calculated 377.42; found 377.51

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customslowly quenched into saturated sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-286fe8e00f3b4f1482a70e9aeca62605
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168652B2

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