Sodium Dithionite → HCID 178436762、化合物

HRID 416829

反応式

HRID 416829 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]([CH:52]([C:54]3[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=3)[CH3:53])[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+].[CH3:68][N:69]1[CH2:74][CH2:73][N:72]([CH2:75][C:76]2[CH:77]=[C:78]([CH:81]=[CH:82][CH:83]=2)[CH:79]=O)[CH2:71][CH2:70]1>C(O)C.CN(C=O)C>[Br:35][C:36]1[C:37]([N:46]2[CH2:51][CH2:50][N:49]([CH:52]([C:54]3[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=3)[CH3:53])[CH2:48][CH2:47]2)=[C:38]2[N:43]=[C:79]([C:78]3[CH:81]=[CH:82][CH:83]=[C:76]([CH2:75][N:72]4[CH2:73][CH2:74][N:69]([CH3:68])[CH2:70][CH2:71]4)[CH:77]=3)[NH:42][C:39]2=[N:40][CH:41]=1

参加物

7

反応物 4

HCID 24489Sodium DithioniteHCID 185257743-[(4-Methylpiperazin-1-yl)methyl]benzaldehydeHCID 468683495-Bromo-3-nitro-4-(4-(1-(pyridin-4-yl)ethyl)piperazin-1-yl)pyridin-2-amineHCID 178482685HCID 178482685、化合物

生成物 1

HCID 178436762HCID 178436762、化合物収率 27.5%

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-3-nitro-4-(4-(1-(pyridin-4-yl)ethyl)piperazin-1-yl)pyridin-2-amine (50 mg, 0.12 mmol), DMF (0.15 mL), ethanol (0.85 mL), 1M Na2S2O4 (3 eq, 0.37 mmol, 0.37 mL) and 3-[(4-methylpiperazin-1-yl)methyl]benzaldehyde (1.1 eq, 0.14 mmol, 29 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 9:1) gave the product (19 mg, 27%) as a colourless solid; δH (500 MHz, DMSO-d6) 1.37 (d, J=6.7 Hz, 3H, CHCH3), 2.17 (s, br, 4H, piperazine N(CH2)2), 2.37-2.48 (m, br, 4H, piperazine N(CH2)2), 2.55-2.58 (m, br, 4H, piperazine N(CH2)2), 2.64-2.67 (m, br, 4H, piperazine N(CH2)2), 3.56 (s, 2H, NCH2Ar), 3.60 (q, J=6.5 Hz, 1H, CHCH3), 3.68 (s, br, 4H, piperazine N(CH2)2), 7.41 (d, J=5.9 Hz, 2H, pyridine H-3 & H-5), 7.43 (d, J=7.7 Hz, 1H, phenyl H-6), 7.50 (t, J=7.7 Hz, 1H, phenyl H-5), 8.06 (d, J=7.7 Hz, 1H, phenyl H-4), 8.14 (s, br, 1H, phenyl H-2), 8.24 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.56 (d, J=5.9 Hz, 1H, pyridine H-2 & H-6), 13.52 (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, 9:1)

出典と根拠

ORDレコード
ord-f4a60a7928a6485bb564ed7c55b236ff
出典データセット
uspto-grants-2012_01
特許番号
US08088761B2

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