Sodium Dithionite → HCID 178488872、化合物

HRID 416851

反応式

HRID 416851 の反応式
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][C:56]([O:59][CH3:60])=[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+].[CH3:69][O:70][C:71]1[CH:76]=[CH:75][C:74]([CH:77]=O)=[CH:73][CH:72]=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][C:56]([O:59][CH3:60])=[CH:57][CH:58]=3)[CH2:48][CH2:47]2)=[C:38]2[N:43]=[C:77]([C:74]3[CH:75]=[CH:76][C:71]([O:70][CH3:69])=[CH:72][CH:73]=3)[NH:42][C:39]2=[N:40][CH:41]=1

参加物

7

反応物 4

HCID 24489Sodium DithioniteHCID 312444-MethoxybenzaldehydeHCID 578971545-Bromo-4-(4-((6-methoxypyridin-3-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amineHCID 178482685HCID 178482685、化合物

生成物 1

HCID 178488872HCID 178488872、化合物収率 56%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

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-4-(4-((6-methoxypyridin-3-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine (30 mg, 0.071 mmol), DMF (0.15 mL), ethanol (0.85 mL), 1M Na2S2O4 (3 eq, 0.21 mmol, 0.21 mL) and 4-methoxybenzene carboxaldehyde (1.1 eq, 0.078 mmol, 10 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 95:5) gave the product (20 mg, 56%) as a colourless solid; δH (500 MHz, DMSO-d6) 2.60 (s, br, 4H, piperazine N(CH2)2), 3.52 (s, 2H, NCH2), 3.64 (t, J=4.5 Hz, 4H, piperazine N(CH2)2), 3.84 (s, 3H, OCH3), 3.85 (s, 3H, OCH3), 6.81 (d, J=8.5 Hz, 1H, methoxypyridine H-5), 7.09 (d, J=8.9 Hz, 2H, methoxyphenyl H-2 & H-6), 7.70 (dd, J=8.5, 2.6 Hz, 1H, methoxypyridine H-4), 8.11 (d, J=2.3 Hz, 1H, methoxypyridine H-2), 8.20 (s, 1H, imidazo[4,5-b]pyridine H-5), 13.34 (s, br, 1H, imidazo[4,5-b]pyridine NH);

後処理

  1. customThis was prepared
  2. concentrationconcentration
  3. customin vacuo and purification by preparative tlc (CH2Cl2-MeOH, 95:5)

出典と根拠

ORDレコード
ord-46fb68b42cca485c956f9154defe97ad
出典データセット
uspto-grants-2012_01
特許番号
US08088761B2

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