Sodium Dithionite → HCID 178468466、化合物

HRID 416764

反応式

HRID 416764 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.[NH2:35][C:36]1[C:41]([N+:42]([O-])=O)=[C:40]([N:45]2[CH2:50][CH2:49][N:48]([CH2:51][C:52]([NH:54][C:55]3[S:56][CH:57]=[CH:58][N:59]=3)=[O:53])[CH2:47][CH2:46]2)[C:39]([Br:60])=[CH:38][N:37]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+].[CH:69]([CH:71]1[CH2:73][CH:72]1[C:74]([O:76][CH2:77][CH3:78])=[O:75])=O>C(O)C.CN(C=O)C>[Br:60][C:39]1[C:40]([N:45]2[CH2:50][CH2:49][N:48]([CH2:51][C:52](=[O:53])[NH:54][C:55]3[S:56][CH:57]=[CH:58][N:59]=3)[CH2:47][CH2:46]2)=[C:41]2[N:42]=[C:69]([CH:71]3[CH2:73][CH:72]3[C:74]([O:76][CH2:77][CH3:78])=[O:75])[NH:35][C:36]2=[N:37][CH:38]=1

参加物

7

反応物 4

HCID 24489Sodium DithioniteHCID 89334Ethyl 2-formylcyclopropanecarboxylateHCID 468678032-(4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamideHCID 178482685HCID 178482685、化合物

生成物 1

HCID 178468466HCID 178468466、化合物収率 25.4%

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 2-(4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide (63 mg, 0.14 mmol), DMF (1.3 mL), ethanol (0.2 mL), 1M Na2S2O4 (3 eq, 0.43 mmol, 0.43 mL) and ethyl 2-formyl-1-cyclopropanecarboxylate (1.1 eq, 0.16 mmol, 0.021 mL). After 16 h, concentration in vacuo and preparation by preparative tlc (EtOAc—CH2Cl2-MeOH, 50:50:2) gave the product (19 mg, 25%) as a colourless solid; 1H-NMR (500 MHz, DMSO-d6) 1.21 (t, J=7.1 Hz, 3H, CH2CH3), 1.56 (app. quintet, J=4.6 Hz, 1H, cyclopropane CHAHB), 1.64-1.67 (m, 1H, cyclopropane CHAHB), 2.26 (app. quintet, J=5.0 Hz, cyclopropane CH), 2.73 (br s, 4H, piperazine N(CH2)2), 3.38 (s, 2H, NCH2CO), 3.57 (br s, 4H, piperazine N(CH2)2), 4.13 (q, J=7.1 Hz, 2H, CH2CH3), 7.23 (d, J=3.5 Hz, 1H, thiazole H-4 or H-5), 7.48 (d, J=3.5 Hz, 1H, thiazole H-4 or H-5), 8.17 (s, 1H, imidazo[4,5-b]pyridine H-5), 11.86 (br s, 1H, CONH or imidazo[4,5-b]pyridine NH), 12.94 (br s, 1H, CONH or imidazo[4,5-b]pyridine NH);

後処理

  1. customThis was prepared
  2. concentrationconcentration
  3. customin vacuo and preparation by preparative tlc (EtOAc—CH2Cl2-MeOH, 50:50:2)

出典と根拠

ORDレコード
ord-08bca1655e354a3ab990309ecff79bfa
出典データセット
uspto-grants-2012_01
特許番号
US08088761B2

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