Pyridine → HCID 131734689, compound

HRID 1772888Notes

Reaction equation

HRID 1772888 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.[C:14]([O:18][C:19](=[O:31])[NH:20][CH2:21][C:22]1[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[C:24]([NH2:30])[N:23]=1)([CH3:17])([CH3:16])[CH3:15].N1C=CC=CC=1.[C:38](N1C=CN=C1)(N1C=CN=C1)=[O:39].C(N(CC)CC)C>C(Cl)Cl.CCOC(C)=O.CN(C=O)C.[Pd]>[C:14]([O:18][C:19](=[O:31])[NH:20][CH2:21][C:22]1[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[C:24]([N:30]2[C:38](=[O:39])[NH:1][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[S:10]2(=[O:12])=[O:11])[N:23]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

10

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 682631,1'-CarbonyldiimidazoleHCID 131734690HCID 131734690, compound

Product 1

HCID 131734689HCID 131734689, compoundYield 46.9%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound (1.03 g, 2.37 mmol) was prepared in three steps from 2-nitrobenzenesulfonyl chloride (1.12 g, 5.05 mmol), tert-butyl(6-amino-3-methoxypyridin-2-yl)methylcarbamate (1.41 g, 5.56 mmol) and pyridine (1.23 mL, 15.2 mmol) in DCM (25 mL) at 0° C. to rt; followed by 10% Pd/C (895 mg) in EtOAc (40 mL); followed by 1,1′-carbonyldiimidazole (2.65 g, 16.4 mmol) and triethylamine (1.14 mL, 8.18 mmol) in DMF (80 mL) using the methods of (IntA17), step 1 and (IntA14), steps 2 and 3.

Sources & evidence

ORD record
ord-8ff4931be5d7495ba5faa12066d8c597
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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