Pyridine → 6-Cyano-pyridine-3-sulfonic acid (6-fluoro-quinolin-8-yl)-amide

HRID 513499Notes

Reaction equation

HRID 513499 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH2:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[C:13]([C:15]1[N:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1)#[N:14].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH:12][S:21]([C:18]3[CH:19]=[N:20][C:15]([C:13]#[N:14])=[CH:16][CH:17]=3)(=[O:22])=[O:23])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 132279926-Fluoroquinolin-8-amine2×HCID 470031906-Cyanopyridine-3-sulfonyl chloride2×

Product 1

HCID 601643066-Cyano-pyridine-3-sulfonic acid (6-fluoro-quinolin-8-yl)-amideYield 26.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 6-fluoroquinolin-8-ylamine (Intermediate 48) (125 mg, 0.77 mmol), 6-cyano-pyridine-3-sulfonyl chloride (Intermediate 19) (187 mg, 0.92 mmol), pyridine (121 mg, 1.54 mmol), DMAP (cat.) and DCM (10 ml) gave the title compound (67 mg, 26%) after purification by column chromatography with n-hexane/DCM (50:50) as the eluent.

Sources & evidence

ORD record
ord-af9ab1f2fc444e40adce37500901a79e
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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