3-Pyridinecarboxaldehyde → HCID 178521202, compound

HRID 416763Notes

Reaction equation

HRID 416763 reaction equation
[Br:1][C:2]1[C:3]([N:20]2[CH2:25][CH2:24][N:23](C(NC3C=CC=CC=3)=O)[CH2:22][CH2:21]2)=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]([CH3:19])C)=CC=3)[NH:8][C:5]2=[N:6][CH:7]=1.NC1C([N+]([O-])=O)=C(N2CCN([CH2:51][C:52]([NH:54][C:55]3[S:56][CH:57]=[CH:58][N:59]=3)=[O:53])CC2)C(Br)=CN=1.[O-]S(S([O-])=O)=O.[Na+].[Na+].N1C=CC=C(C=O)C=1>CN(C=O)C>[Br:1][C:2]1[C:3]([N:20]2[CH2:25][CH2:24][N:23]([CH2:51][C:52]([NH:54][C:55]3[S:56][CH:57]=[CH:58][N:59]=3)=[O:53])[CH2:22][CH2:21]2)=[C:4]2[N:10]=[C:9]([C:11]3[CH:19]=[N:17][CH:14]=[CH:15][CH:16]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 103713-PyridinecarboxaldehydeHCID 24489Sodium DithioniteHCID 468678032-(4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamideHCID 178482685HCID 178482685, compound

Product 1

HCID 178521202HCID 178521202, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 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 2-(4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide (50 mg, 0.11 mmol), DMF (1 mL), 1M Na2S2O4 (3 eq, 0.33 mmol, 0.33 mL) and 3-pyridinecarboxaldehyde (1.05 eq, 0.12 mmol, 0.011 mL). After 16 h, the DMF was removed in vacuo, the residue taken up in water (2 mL) and extracted with EtOAc (2×3 mL) and CH2Cl2 (2×3 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the product (21 mg, 38%) as a pale brown solid; 1H-NMR (500 MHz, DMSO-d6) 3.30 (hidden by water-in-DMSO peak, 6H, NCH2CO and piperazine N(CH2)2), 3.89 (br s, 4H, piperazine N(CH2)2), 7.28 (br s, 1H, thiazole H-4 or H-5), 7.52 (d, J=3.5 Hz, 1H, thiazole H-4 or H-5), 7.60 (dd, J=7.9, 4.8 Hz, 1H, pyridine H-5), 8.32 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.52 (d, br, J=8.0 Hz, 1H, pyridine H-4), 8.71 (d, br, J=4.7 Hz, 1H, pyridine H-6), 9.38 (s, 1H, pyridine H-2), 13.80 (s, br, 1H, imidazo[4,5-b]pyridine NH);

Workup

  1. customThis was prepared
  2. customthe DMF was removed in vacuo
  3. extractionextracted with EtOAc (2×3 mL) and CH2Cl2 (2×3 mL)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1968b7815af24751b1aac01bb3524802
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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