Ethanol → HCID 178521210, 화합물

HRID 416946

반응식

HRID 416946 반응식
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]([NH:20][C:21]3[S:22][CH:23]=[CH:24][N:25]=3)=[O:19])[CH2:13][CH2:12]2)[C:5]([Cl:26])=[CH:4][N:3]=1.CCO.[OH:30][CH2:31][CH2:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(Cl)Cl.N.CN(C=O)C>[Cl:26][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]([NH:20][C:21]3[S:22][CH:23]=[CH:24][N:25]=3)=[O:19])[CH2:13][CH2:12]2)=[C:7]2[N:8]=[C:38]([C:37]3[CH:36]=[CH:35][C:34]([O:33][CH2:32][CH2:31][OH:30])=[CH:41][CH:40]=3)[NH:1][C:2]2=[N:3][CH:4]=1

참가 물질

8

반응물 4

HCID 702EthanolHCID 24489Sodium DithioniteHCID 89178Benzaldehyde, 4-(2-hydroxyethoxy)-HCID 468678042-(4-(2-amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide

생성물 1

HCID 178521210HCID 178521210, 화합물

시약·촉매·용매 3

HCID 222Ammonia촉매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
85 °C

실험 절차

To a mixture of 2-(4-(2-amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide (0.060 g, 0.15 mmol, 1 eq), EtOH (2.6 mL) and DMF (0.35 mL), 4-(2-hydroxyethoxy)benzaldehyde (0.028 g, 0.17 mmol, 1.1 eq) was added followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.45 mL, 0.45 mmol). The reaction mixture was heated at 85° C. for 24 h, then allowed to cool to room temperature and diluted with DCM and a few drops of aqueous NH3 until complete dissolution was observed. This solution was deposited on two preparative silica TLC plates and eluted with DCM/MeOH (v/v; 94:6). The title compound was obtained after trituration with diethyl ether as a off-white solid (0.021 g, 27%); 1H-NMR (500 Mz, DMSO-d6): 2.74-2.81 (m, 4H, piperazine N(CH2)2), 3.40 (s, 2H, NCH2), 3.69-3.79 (m, 6H, piperazine N(CH2)2 and OCH2), 4.07 (t, J=5.0 Hz, 2H, OCH2), 4.88 (t, J=5.5 Hz, 1H, OH), 7.10 (d, J=9.0 Hz, 2H, ArH, C6H4), 7.23 (d, J=3.5 Hz, 1H) and 7.49 (d, J=3.5 Hz, 1H) (thiazole H-4, H-5), 8.08 (s, 1H, imidazo[4,5-b]pyridine 5-H), 8.12 (d, J=9.0 Hz, 2H, ArH, C6H4); LC (Method B)-MS (ESI, m/z) 3.69 min—514/516 [(M+H)+, Cl isotopic pattern].

후처리

  1. additionwas added
  2. temperatureto cool to room temperature
  3. washeluted with DCM/MeOH (v/v; 94:6)

출처 및 근거

ORD 기록
ord-c56f91284e964cc2ba0ebd2c5c1876fd
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088761B2

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