2-Aminothiazole → 2-(3-(difluoromethyl)phenyl)-N-(thiazol-2-yl)quinoline-8-carboxamide

HRID 2359408Notes

Reaction equation

[F:1][CH:2]([F:22])[C:3]1[CH:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[C:12]([C:19]([OH:21])=O)[CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1.[S:23]1[CH:27]=[CH:26][N:25]=[C:24]1[NH2:28].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[F:1][CH:2]([F:22])[C:3]1[CH:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[C:12]([C:19]([NH:28][C:24]4[S:23][CH:27]=[CH:26][N:25]=4)=[O:21])[CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 2-(3-(difluoromethyl)phenyl)quinoline-8-carboxylic acid (250 mg, 0.84 mmol), thiazol-2-amine (84 mg, 1.2 mmol), HATU (0.64 g, 1.68 mmol) and DIPEA (0.22 g, 1.68 mmol) in DMF (25 mL) was stirred at 40° C. for 12 hours. A saturated solution of NaHCO3 (5 mL) was added and the mixture was filtered, the residue was washed with methanol (2×5 mL) and solid was dried in vacuo to give 2-(3-(difluoromethyl)phenyl)-N-(thiazol-2-yl)quinoline-8-carboxamide as a solid. (125 mg, 39% yield) MS (ESI) calcd for C20H13F2N3OS (m/z): 381.07. found: 382 [M+1].

Workup

filtrationthe mixture was filtered
washthe residue was washed with methanol (2×5 mL) and solid
customwas dried in vacuo

Sources & evidence

ORD record: ord-56f6e310afc34fdc9a48041e0bd185c7
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685970B2

Reaction notes

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