3-Fluoro-5-aminoquinoline → N-(4-bromo-3-(1H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(3-fluoroquinolin-5-yl)acetamide

HRID 2098034Notes

Reaction equation

HRID 2098034 reaction equation
FC1C=NC2C=CC=C(N)C=2C=1.Cl.[F:14][C:15]1[CH:16]=[N:17][C:18]2[C:23]([CH:24]=1)=[C:22]([CH2:25][C:26]([OH:28])=O)[CH:21]=[CH:20][CH:19]=2.[Br:29][C:30]1[C:31]([C:36]2[NH:40][CH:39]=[N:38][N:37]=2)=[C:32]([NH2:35])[S:33][CH:34]=1>>[Br:29][C:30]1[C:31]([C:36]2[N:40]=[CH:39][NH:38][N:37]=2)=[C:32]([NH:35][C:26](=[O:28])[CH2:25][C:22]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:23]=2[CH:24]=[C:15]([F:14])[CH:16]=[N:17]3)[S:33][CH:34]=1

Participants

4

Reactant 3

HCID 1546773-Fluoro-5-aminoquinolineHCID 687542642-(3-Fluoroquinolin-5-yl)acetic acid hydrogen chlorideHCID 178509325HCID 178509325, compound

Product 1

HCID 178520203N-(4-bromo-3-(1H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(3-fluoroquinolin-5-yl)acetamide

Procedure

The title compound was prepared by converting 3-fluoroquinolin-5-amine (850 mg, 5.24 mmol) into 2-(3-fluoroquinolin-5-yl)acetic acid hydrogen chloride (76 mg, 315 umol) and reaction with 4-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amine (34 mg, 139 umol) as outlined in Example 1.68., above. Method [8] retention time 2.46 min by HPLC (M+206). 1H NMR (300 MHz, CDCl3) δ 12.35 (s, 1H), 8.89 (d, J=2.7 Hz, 1H), 8.26 (d, J=8.7 Hz, 1H), 8.07 (dd, J=9.3 and 2.7 Hz, 1H), 7.83 (m, 1H), 7.74 (d, J=6.9 Hz, 1H), 7.59 (s, 1H), 6.93 (s, 1H), 4.33 (s, 2H).

Sources & evidence

ORD record
ord-647abd10c4ca486391987149a0085638
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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