6-Methoxy-8-quinolinamine → HCID 68183303, compound

HRID 513642Notes

Reaction equation

HRID 513642 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([NH2:13])[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.Cl[S:15]([OH:18])(=O)=[O:16].P(Cl)(Cl)(Cl)(Cl)Cl.CCN(C(C)C)C(C)C.[F:34][C:35]1[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[C:36]=1[NH2:37]>>[F:34][C:35]1[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[C:36]=1[NH:37][S:15]([NH:13][C:11]1[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[CH:6]2)(=[O:18])=[O:16]

Participants

6

Reactant 5

HCID 70236-Methoxy-8-quinolinamine2×HCID 24638Chlorosulfonic acidHCID 24819Phosphorus pentachlorideHCID 796472,6-DifluoroanilineHCID 81531Diisopropylethylamine

Product 1

HCID 68183303HCID 68183303, compoundYield 4%

Procedure

In the similar fashion using route 19 general procedure 42, 6-methoxyquinolin-8-amine (Intermediate 23) (200 mg, 1.15 mmol), TEA (170 mg, 1.72 mmol), chlorosulfonic acid (150 mg, 1.27 mmol), PCl5 (260 mg, 1.72 mmol), DIPEA (300 mg, 2.23 mmol), 2,6-difluoroaniline (600 mg, 4.6 mmol) gave the title compound (15 mg, 4%) after purification by column chromatography with DCM/MeOH (1:0-97:3) as the eluent.

Sources & evidence

ORD record
ord-f378710d64b44f27a7c6bf544d817763
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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