Sodium Dithionite → HCID 178521207, compound

HRID 416948Notes

Reaction equation

HRID 416948 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.[N:27]1([CH2:33][CH2:34][O:35][C:36]2[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=2)[CH:39]=O)[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>CCO.CN(C=O)C.C(Cl)Cl.N>[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:41]=[CH:42][CH:43]=[C:36]([O:35][CH2:34][CH2:33][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[CH:37]=3)[NH:1][C:2]2=[N:3][CH:4]=1

Participants

8

Reactant 3

HCID 24489Sodium DithioniteHCID 71646203-(2-Morpholin-4-ylethoxy)benzaldehydeHCID 468678042-(4-(2-amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide

Product 1

HCID 178521207HCID 178521207, compound

Reagents, catalysts & solvents 4

HCID 222AmmoniaCatalystHCID 702EthanolSolventHCID 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 (0.060 g, 0.15 mmol, 1 eq) in EtOH (2.6 mL) and DMF (0.35 mL), 3-(2-morpholin-4-ylethoxy)benzaldehyde (0.039 g, 0.17 mmol, 1.1 eq) was added followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.45 mL, 0.45 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; 94:6). The title compound was obtained after trituration with diethyl ether as a pale yellow solid (0.018 g, 21%); 1H-NMR (500 Mz, DMSO-d6): 2.68-2.85 (m, 6H), 3.41 (s, 2H, NCH2CO), 3.55-3.65 (m, 4H), 3.71-3.80 (m, 4H), 4.12-4.25 (s, 2H), 7.06-7.12 (m, 1H), 7.23 (d, J=3.5 Hz, 1H, thiazole H-5 or thiazole H-4), 7.40-7.50 (m, 2H, thiazole H-4 or thiazole H-4 and ArH), 7.75-7.82 (m, 2H, ArH), 8.13 (s, 1H, imidazo[4,5-b]pyridine 5-H), 11.70-12.10 (br s, 1H, NHCO), 13.18 (br s, 1H, imidazo[4,5-b]pyridine N—H); LC (Method B)-MS (ESI, m/z) 2.62 min—583/585 [(M+H)+, Cl isotopic pattern].

Workup

  1. additionwas added
  2. temperatureto cool to room temperature
  3. washeluted with DCM/MeOH (v/v; 94:6)

Sources & evidence

ORD record
ord-9331357f27314fb785dc34b6bbbb1b29
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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