Sodium hydride → 8-[5-(3-Chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine

HRID 732080노트

반응식

HRID 732080 반응식
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]3[CH2:14][CH2:15][CH2:16][NH:17][C:12]3=[N:11][N:10]=2)=[CH:5][CH:4]=1.[Cl:18][C:19]1[CH:20]=[C:21]([C:25]2[O:29][N:28]=[C:27]([CH2:30]Cl)[N:26]=2)[CH:22]=[CH:23][CH:24]=1>CN(C=O)C>[Cl:18][C:19]1[CH:20]=[C:21]([C:25]2[O:29][N:28]=[C:27]([CH2:30][N:17]3[CH2:16][CH2:15][CH2:14][N:13]4[C:9]([C:6]5[CH:7]=[CH:8][N:3]=[CH:4][CH:5]=5)=[N:10][N:11]=[C:12]34)[N:26]=2)[CH:22]=[CH:23][CH:24]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 100825203-(Chloromethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazoleHCID 1361179203-Pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine

생성물 1

HCID 670707678-[5-(3-Chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine수율 32.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

32 mg (1.31 mmol) NaH was added to a solution of 193 mg (0.96 mmol) 3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine in 10 ml DMF at room temperature. After 10 min 200 mg (0.87mmol) 5-(3-chloro-phenyl)-3-chloromethyl-[1,2,4]oxadiazole was added to the reaction mixture. The reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with NH4Cl(sat) and extracted twice with EtOAc. The combined organic phases were washed with water, dried and concentrated. Flashchromatography (CH2Cl2/MeOH 20:1) afforded 111 mg (32%) of a white solid. 1H NMR (CDCl3), d (ppm): 2.24 (m, 2 H), 3.57 (m, 2 H) 4.15 (m, 2 H) 5.01 (s, 2 H) 7.46 (t, 1 H) 7.56 (d, 1 H) 7.62 (d, 2 H) 7.99 (d, 1 H) 8.10 (s, 1 H) 8.70 (d, 2 H).

후처리

  1. extractionextracted twice with EtOAc
  2. washThe combined organic phases were washed with water
  3. customdried
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-fdaa5fd19621477394410c05126284b4
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585881B2

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