3-Chloro-2-methylaniline → HCID 68183460, compound

HRID 513640Notes

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.[Cl:25][C:26]1[C:27]([CH3:33])=[C:28]([CH:30]=[CH:31][CH:32]=1)[NH2:29].CCN(C(C)C)C(C)C>>[Cl:25][C:26]1[C:27]([CH3:33])=[C:28]([NH:29][S:15]([NH:13][C:11]2[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]3[C:10]=2[N:9]=[CH:8][CH:7]=[CH:6]3)(=[O:18])=[O:16])[CH:30]=[CH:31][CH:32]=1

Participants

Reactant 5

HCID 68943-Chloro-2-methylaniline

HCID 70236-Methoxy-8-quinolinamine2×

HCID 24638Chlorosulfonic acid

HCID 24819Phosphorus pentachloride

HCID 81531Diisopropylethylamine

Product 1

HCID 68183460HCID 68183460, compoundYield 2.3%

Procedure

In a similar fashion using route 19 general procedure 42, 6-methoxyquinolin-8-amine (Intermediate 23) (300 mg, 1.7 mmol), chlorosulfonic acid (120 μl, 1.8 mmol), PCl5 (370 mg, 1.8 mmol), TEA (360 μl, 2.5 mmol), 3-chloro-2-methylaniline (810 μl, 6.8 mmol) and DIPEA (600 μl, 3.4 mmol) gave the title compound (15 mg, 2%) after purification by column chromatography with DCM/n-hexane (1:1) as the eluent, followed by recrystallisation from EtOAc/n-hexane and then further purification by column chromatography with n-hexane/EtOAc (4:1) as the eluent.

Sources & evidence

ORD record: ord-f5ebefbde0454456a3cad92eb1410142
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

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