Sodium Dithionite → HCID 178506177, compound

HRID 416861Notes

Reaction equation

HRID 416861 reaction equation
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]([CH2:52][C:53]3[CH:54]=[N:55][C:56]([C:59]([F:62])([F:61])[F:60])=[CH:57][CH:58]=3)[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+].[N:71]1([C:77]2[CH:84]=[CH:83][C:80]([CH:81]=O)=[CH:79][CH:78]=2)[CH2:76][CH2:75][O:74][CH2:73][CH2:72]1>C(O)C.CN(C=O)C>[Br:35][C:36]1[C:37]([N:46]2[CH2:51][CH2:50][N:49]([CH2:52][C:53]3[CH:54]=[N:55][C:56]([C:59]([F:62])([F:61])[F:60])=[CH:57][CH:58]=3)[CH2:48][CH2:47]2)=[C:38]2[N:43]=[C:81]([C:80]3[CH:79]=[CH:78][C:77]([N:71]4[CH2:76][CH2:75][O:74][CH2:73][CH2:72]4)=[CH:84][CH:83]=3)[NH:42][C:39]2=[N:40][CH:41]=1

Participants

7

Reactant 4

HCID 24489Sodium DithioniteHCID 2913494-MorpholinobenzaldehydeHCID 57897304HCID 57897304, compoundHCID 178482685HCID 178482685, compound

Product 1

HCID 178506177HCID 178506177, compoundYield 23.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

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-((6-(trifluoromethyl)pyridin-3-yl)methyl)piperazin-1-yl)pyridin-2-amine (20 mg, 0.043 mmol), DMF (0.15 mL), ethanol (0.85 mL), 1M Na2S2O4 (3 eq, 0.13 mmol, 0.13 mL) and 4-morpholin-4-yl-benzaldehyde (1.1 eq, 0.048 mmol, 9 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 95:5) gave the product (6 mg, 23%) as a pale yellow solid; δH (500 MHz, DMSO-d6) 2.65 (t, J=4.4 Hz, 4H, piperazine N(CH2)2), 3.24 (t, J=4.9 Hz, 4H, morpholine N(CH2)2), 3.66 (t, J=4.5 Hz, 4H, piperazine N(CH2)2), 3.73 (s, 2H, CH2), 3.76 (t, J=4.9 Hz, 4H, morpholine O(CH2)2), 7.06 (d, J=9.0 Hz, 2H, phenyl H-3 & H-5), 7.90 (d, br, J=8.0 Hz, 1H, pyridine H-5), 8.04 (d, J=9.0 Hz, 2H, phenyl H-2 & H-6), 8.08 (dd, J=8.1, 1.0 Hz, 1H, pyridine H-4), 8.18 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.77 (s, br, 1H, pyridine H-2), 13.23 (s, br, 1H, imidazo[4,5-b]pyridine NH);

Workup

  1. customThis was prepared
  2. concentrationconcentration
  3. customin vacuo and purification by preparative tlc (CH2Cl2-MeOH, 95:5)

Sources & evidence

ORD record
ord-4490965350484c5d9a96e5fa010ac134
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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