4-(Dimethylamino)Benzaldehyde → HCID 178482663、化合物

HRID 416747ノート

反応式

HRID 416747 の反応式
[Br:1][C:2]1[C:3]([N:12]2[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-])=O)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:27][N:28]([CH3:37])[C:29]1[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][CH:30]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(O)C>[Br:1][C:2]1[C:3]([N:12]2[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:14][CH2:13]2)=[C:4]2[N:9]=[C:33]([C:32]3[CH:35]=[CH:36][C:29]([N:28]([CH3:37])[CH3:27])=[CH:30][CH:31]=3)[NH:8][C:5]2=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 74794-(Dimethylamino)BenzaldehydeHCID 24489Sodium DithioniteHCID 57897211HCID 57897211、化合物

生成物 1

HCID 178482663HCID 178482663、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

To a mixture of 5-bromo-4-(4-(4-fluorobenzyl)-1,4-diazepan-1-yl)-3-nitropyridin-2-amine (0.047 g, 0.11 mmol), ethanol (4 ml), and 4-dimethylaminobenzaldehyde (0.021 g, 0.14 mmol) was added a freshly prepared aqueous solution of Na2S2O4 (1M; 0.44 ml, 0.44 mmol). The reaction mixture was heated at 70° C. for 4.5 h, then allowed to cool to room temperature and the solvents were removed in vacuo. The residue was absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column which was eluted with 0 to 5% methanol in ethyl acetate/dichloromethane (v/v; 1:1). The title compound was obtained as a yellow solid (0.020 g, 35%); 1H-NMR (500 MHz, DMSO-d6) 2.00 (m, 2H), 2.75-2.85 (m, 4H) and 3.86 (m, 4H) (homopiperazine protons), 2.99 (s, 6H, N(CH3)2), 3.66 (s, 2H, N—CH2), 6.82 (d, J=9.00 Hz, 2H) and 8.00 (d, J=8.84 Hz, 2H) (3,5-C6H4NMe2 and 2,6-C6H4—NMe2), 7.14 (t, J=8.93 Hz, 2H) and 7.39 (dd, J=8.13, 5.42 Hz, 2H) (3,5-ArH and 2,6-ArH), 8.11 (s, 1H, imidazo[4,5-b]pyridine 5-H), 13.08 (s, 1H, imidazo[4,5-b]pyridine N—H);

後処理

  1. temperatureto cool to room temperature
  2. customthe solvents were removed in vacuo
  3. customThe residue was absorbed on silica gel
  4. washwas eluted with 0 to 5% methanol in ethyl acetate/dichloromethane (v/v; 1:1)

出典と根拠

ORDレコード
ord-b8fd05818be3402cb74af0f829a1e517
出典データセット
uspto-grants-2012_01
特許番号
US08088761B2

反応ノート

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