Pyridine → HCID 90054779, compound

HRID 1772890Notes

Reaction equation

HRID 1772890 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-])=O.Cl.[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[N:20]=[C:19]([NH2:25])[CH:18]=1.N1C=CC=CC=1.[C:32](N1C=CN=C1)(N1C=CN=C1)=[O:33].C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C.[Fe].C(O)(=O)C>[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[N:20]=[C:19]([N:25]2[C:32](=[O:33])[NH:1][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[S:10]2(=[O:12])=[O:11])[CH:18]=1

Participants

10

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 682631,1'-CarbonyldiimidazoleHCID 57363184HCID 57363184, compound

Product 1

HCID 90054779HCID 90054779, compoundYield 9.7%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound (316 mg, 0.94 mmol) was prepared in three steps from 2-nitrobenzenesulfonyl chloride (2.15 g, 9.7 mmol), 4,6-dimethoxypyridin-2-amine hydrochloride (2.04 g, 10.7 mmol) and pyridine (2.35 mL, 29.1 mmol) in DCM (35 mL) at rt; followed by Fe powder (1.38 g, 24.7 mmol) and acetic acid (15 mL); followed by 1,1′-carbonyldiimidazole (1.62 g, 10.0 mmol) and triethylamine (0.70 mL, 5.0 mmol) in DMF (10.0 mL) using the methods of (IntA1), step 1, (IntA17), step 2 and (IntA14), step 3.

Sources & evidence

ORD record
ord-8c86f9c9badf4b26ae238efa13878f32
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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