Sodium Dithionite → HCID 178483864, 화합물

HRID 416844

반응식

HRID 416844 반응식
BrC1C(N2CCN(C(NC3C=CC=CC=3)=O)CC2)=C2N=C(C3C=CC(N(C)C)=CC=3)NC2=NC=1.[Br:35][C:36]1[C:37]([N:46]2[CH2:51][CH2:50][N:49]([CH2:52][C:53]3[CH:54]=[N:55][CH:56]=[CH:57][CH:58]=3)[CH2:48][CH2:47]2)=[C:38]([N+:43]([O-])=O)[C:39]([NH2:42])=[N:40][CH:41]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+].[CH3:67][N:68]([CH3:80])[CH2:69][CH2:70][O:71][C:72]1[CH:79]=[CH:78][C:75]([CH:76]=O)=[CH:74][CH:73]=1>C(O)C.CN(C=O)C>[Br:35][C:36]1[C:37]([N:46]2[CH2:51][CH2:50][N:49]([CH2:52][C:53]3[CH:54]=[N:55][CH:56]=[CH:57][CH:58]=3)[CH2:48][CH2:47]2)=[C:38]2[N:43]=[C:76]([C:75]3[CH:78]=[CH:79][C:72]([O:71][CH2:70][CH2:69][N:68]([CH3:67])[CH3:80])=[CH:73][CH:74]=3)[NH:42][C:39]2=[N:40][CH:41]=1

참가 물질

7

반응물 4

HCID 24489Sodium DithioniteHCID 84823p-(2-(Dimethylamino)ethoxy)benzaldehydeHCID 468687795-Bromo-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amineHCID 178482685HCID 178482685, 화합물

생성물 1

HCID 178483864HCID 178483864, 화합물수율 24.5%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6228Dimethylformamide용매

실험 절차

This was prepared using the same procedure as for 4-(6-bromo-2-(4-(dimethylamino)phenyl)-3H-imidazo[4,5-b]pyridin-7-yl)-N-phenylpiperazine-1-carboxamide, but here using 5-bromo-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amine (30 mg, 0.076 mmol), DMF (0.15 mL), ethanol (0.85 mL), 1M Na2S2O4 (3 eq, 0.23 mmol, 0.23 mL) and 4-(2-(dimethylamino)ethoxy)benzaldehyde (1.2 eq, 0.091 mmol, 18 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 85:15) gave the product (10 mg, 23%) as a colourless solid; δH (500 MHz, DMSO-d6) 2.23 (s, 6H, N(CH3)2), 2.62 (s, br, 4H, piperazine N(CH2)2), 2.65 (t, J=5.8 Hz, 2H, Me2NCH2), 3.61 (s, 2H, NCH2), 3.65 (t, J=4.4 Hz, 4H, piperazine N(CH2)2), 4.13 (t, J=5.8 Hz, 2H, OCH2), 7.09 (d, J=8.8 Hz, 2H, phenyl H-3 & H-5), 7.39 (dd, J=7.7, 4.8 Hz, 1H, pyridine H-5), 7.78 (dt, J=7.8, 1.7 Hz, 1H, pyridine H-4), 8.11 (d, J=8.8 Hz, 2H, phenyl H-2 & H-6), 8.20 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.49 (dd, J=4.8, 1.4 Hz, 1H, pyridine H-6), 8.56 (d, J=1.4 Hz, 1H, pyridine H-2), 13.34 (s, br, 1H, imidazo[4,5-b]pyridine NH);

후처리

  1. customThis was prepared
  2. concentrationconcentration
  3. customin vacuo and purification by preparative tlc (CH2Cl2-MeOH, 85:15)

출처 및 근거

ORD 기록
ord-652c6f0ab421402c9afaae778489d1e0
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088761B2

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