Sodium Dithionite → 6-Bromo-2-(3-((4-methylpiperazin-1-yl)methyl)phenyl)-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3h-imidazo[4,5-b]pyridine

HRID 416785

反応式

HRID 416785 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][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]1[CH2:73][CH2:72][N:71]([CH2:74][C:75]2[CH:76]=[C:77]([CH:80]=[CH:81][CH:82]=2)[CH:78]=O)[CH2:70][CH2:69]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:78]([C:77]3[CH:80]=[CH:81][CH:82]=[C:75]([CH2:74][N:71]4[CH2:72][CH2:73][N:68]([CH3:67])[CH2:69][CH2:70]4)[CH:76]=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 468687795-Bromo-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amineHCID 178482685HCID 178482685、化合物

生成物 1

HCID 1784808196-Bromo-2-(3-((4-methylpiperazin-1-yl)methyl)phenyl)-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3h-imidazo[4,5-b]pyridine収率 18%

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-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amine (75 mg, 0.19 mmol), DMF (0.85 mL), ethanol (0.15 mL), 1M Na2S2O4 (3 eq, 0.57 mmol, 0.57 mL) and 3-[(4-methylpiperazin-1-yl)methyl]benzaldehyde (1.1 eq, 0.21 mmol, 46 mg). After 6 h, concentration in vacuo and preparation by preparative tlc (CH2Cl2-MeOH, 9:1) gave the product (19 mg, 18%) as a colourless solid; 1H-NMR (500 MHz, DMSO-d6) 2.15 (s, 3H, NCH3), 2.50 (hidden by DMSO peak, 4H, piperazine N(CH2)2), 2.64 (br, 4H, piperazine N(CH2)2), 3.30 (hidden by watert-in-DMSO peak, 4H, piperazine N(CH2)2), 3.56 (s, 2H, CH2), 3.63 (s, 2H, CH2), 3.68 (t, J=4.8 Hz, 4H, piperazine N(CH2)2), 7.40 (dd, J=7.8, 4.8 Hz, 1H, pyridine H-5), 7.43 (d, J=7.8 Hz, 1H, phenyl H-4 or H-6), 7.50 (t, J=7.8 Hz, 1H, phenyl H-5), 7.79 (d, br, J=7.7 Hz, 1H, pyridine H-4), 8.07 (d, br, J=8.5 Hz, 1H, phenyl H-4 or H-6), 8.14 (s, br, 1H, phenyl H-2), 8.25 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.50 (dd, J=4.8, 1.5 Hz, 1H, pyridine H-6), 8.57 (d, J=1.6 Hz, 1H, pyridine H-2), 13.52 (br s, 1H, imidazo[4,5-b]pyridine NH);

後処理

  1. customThis was prepared
  2. concentrationconcentration
  3. customin vacuo and preparation by preparative tlc (CH2Cl2-MeOH, 9:1)

出典と根拠

ORDレコード
ord-6f5fb2bad98c4cbeaf1180b8a2de6e02
出典データセット
uspto-grants-2012_01
特許番号
US08088761B2

関連ノート

読み込み中…