Ethanol → HCID 178483865, compound

HRID 416949Notes

Reaction equation

HRID 416949 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]([NH:20][C:21]3[S:22][CH:23]=[CH:24][N:25]=3)=[O:19])[CH2:13][CH2:12]2)[C:5]([Cl:26])=[CH:4][N:3]=1.CCO.[CH3:30][N:31]([CH3:43])[CH2:32][CH2:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(Cl)Cl.N.CN(C=O)C>[Cl:26][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]([NH:20][C:21]3[S:22][CH:23]=[CH:24][N:25]=3)=[O:19])[CH2:13][CH2:12]2)=[C:7]2[N:8]=[C:39]([C:38]3[CH:37]=[CH:36][C:35]([O:34][CH2:33][CH2:32][N:31]([CH3:30])[CH3:43])=[CH:42][CH:41]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 24489Sodium DithioniteHCID 84823p-(2-(Dimethylamino)ethoxy)benzaldehydeHCID 468678042-(4-(2-amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide

Product 1

HCID 178483865HCID 178483865, compound

Reagents, catalysts & solvents 3

HCID 222AmmoniaCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 2-(4-(2-amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide (0.050 g, 0.13 mmol, 1 eq), EtOH (2.2 mL) and DMF (0.29 mL), 4-(2-dimethylaminoethoxy)benzaldehyde (0.027 g, 0.14 mmol, 1.1 eq) was added followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.38 mL, 0.38 mmol). The reaction mixture was heated at 85° C. for 24 h, then allowed to cool to room temperature and diluted with DCM and a few drops of aqueous NH3 until complete dissolution was observed. This solution was deposited on two preparative silica TLC plates and eluted with DCM/MeOH (v/v; 92:8). The title compound was obtained after trituration with diethyl ether as a pale yellow solid (0.010 g, 15%); 1H-NMR (500 Mz, DMSO-d6): 2.24 (s, 6H, NMe2), 2.66 (t, J=5.5 Hz, 2H, CH2NMe2), 2.75-2.80 (m, 4H, piperazine N(CH2)2), 3.40 (s, 2H, NCH2CO), 3.70-3.76 (m, 4H), 4.13 (t, J=5.8 Hz, 2H, CH2O), 7.10 (d, J=8.5 Hz, 2H, ArH C6H4), 7.23 (d, J=4.0 Hz, 1H) and 7.49 (d, J=3.50 Hz, 1H) (thiazole H-4, H-5), 8.04-8.11 (m, 3H, imidazo[4,5-b]pyridine 5-H and ArH C6H4), 11.88 (br s, 1H, NHCO), 13.24 (br s, 1H, imidazo[4,5-b]pyridine N—H); LC (Method B)-MS (ESI, m/z) 3.63 min—587/589 [(M+H)+, Cl isotopic pattern].

Workup

  1. additionwas added
  2. temperatureto cool to room temperature
  3. washeluted with DCM/MeOH (v/v; 92:8)

Sources & evidence

ORD record
ord-d061c6d65c95445ab809e38c676d8d94
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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