1,2-Dichloroethane → 9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8(7H)-one

HRID 221983

반응식

HRID 221983 반응식
[NH:1]([C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7](=[O:13])[NH:8]2)[NH2:2].[N:20]1[CH:25]=[CH:24][CH:23]=[N:22][C:21]=1[C:26](O)=O.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C.CC(O)=O>[C:14]1([C:6]2[C:7](=[O:13])[NH:8][C:9]3[CH:10]=[CH:11][N:12]4[C:26]([C:21]5[N:22]=[CH:23][CH:24]=[CH:25][N:20]=5)=[N:2][N:1]=[C:3]4[C:4]=3[CH:5]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 12626245Pyrimidine-2-carboxylic acidHCID 670760575-hydrazino-3-phenyl-1,6-naphthyridine-2(1H)-one

생성물 1

HCID 1363526579-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8(7H)-one

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

To a mixture of 5-hydrazino-3-phenyl-1,6-naphthyridine-2(1H)-one (2-3) (1.4 g, 5.55 mmol), 2-pyrimidinecarboxylic acid (0.69 g, 5.55 mmol), HOBt (0.85 g, 5.55 mmol), and DIPEA (0.97 mL, 5.55 mmol) in DMF (50 mL) was added EDC (1.23 g, 6.66 mmol). After stirring for overnight, AcOH (5 mL) was added, and the mixture was heated under microwave irradiation at 150° C. for 15 minutes. The solvent was removed under reduced pressure, and the residue was diluted with MeOH, and added water. The resulting solid was collected by filtration to give 9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8(7H)-one (2-4) as a colorless solid.

후처리

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with MeOH
  3. additionadded water
  4. filtrationThe resulting solid was collected by filtration

출처 및 근거

ORD 기록
ord-b6e29215f372433f9ed8b85f18948545
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207169B2

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