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

HRID 416781ノート

反応式

HRID 416781 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][O:69][C:70]1[CH:75]=[CH:74][C:73]([CH:76]=O)=[CH:72][CH:71]=1>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:76]([C:73]3[CH:74]=[CH:75][C:70]([O:69][CH3:68])=[CH:71][CH:72]=3)[NH:42][C:39]2=[N:40][CH:41]=1

参加物

6

反応物 4

HCID 24489Sodium DithioniteHCID 312444-MethoxybenzaldehydeHCID 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 1784888896-Bromo-2-(4-methoxyphenyl)-7-(4-(1-(pyridin-4-yl)ethyl)piperazin-1-yl)-3h-imidazo[4,5-b]pyridine収率 42%

試薬・触媒・溶媒 1

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 (30 mg, 0.074 mmol), DMF (1 mL), 1M Na2S2O4 (3 eq, 0.22 mmol, 0.22 mL) and 4-methoxybenzene carboxaldehyde (1.05 eq, 0.077 mmol, 0.0096 mL). After 16 h, filtration of the precipitate and washing with ethanol (1 mL) and cold water (1 mL) gave the product (15 mg, 42%) as a pale yellow solid; 1H-NMR (500 MHz, DMSO-d6) 1.37 (d, J=6.7 Hz, 3H, CHCH3), 2.56-2.65 (2 m, 4H, piperazine N(CH2)2), 3.58 (q, J=6.9 Hz, 1H, CHCH3), 3.66 (br s, 4H, piperazine N(CH2)2), 3.85 (s, 3H, OCH3), 7.11 (d, J=8.8 Hz, 2H, methoxyphenyl), 7.40 (d, J=5.4 Hz, 2H, pyridine H-3 & H-5), 8.14 (d, J=8.5 Hz, 2H, methoxyphenyl), 8.20 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.55 (d, J=5.4 Hz, 2H, pyridine H-2 & H-6), 13.40 (br s, 1H, imidazo[4,5-b]pyridine NH);

後処理

  1. customThis was prepared
  2. filtrationfiltration of the precipitate
  3. washwashing with ethanol (1 mL) and cold water (1 mL)

出典と根拠

ORDレコード
ord-707de391bbea4e78b31fee44f4512e0b
出典データセット
uspto-grants-2012_01
特許番号
US08088761B2

反応ノート

読み込み中…