8-Aminoquinoline → HCID 71677884, compound

HRID 1469841Notes

Reaction equation

HRID 1469841 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH2:11])[CH:4]=[CH:3][CH:2]=1.[Cl:12][C:13]1[C:18]([C:19](O)=[O:20])=[C:17]([F:22])[C:16]([CH2:23][NH:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:15][CH:14]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:12][C:13]1[C:18]([C:19]([NH:11][C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[N:1]=[CH:2][CH:3]=[CH:4]3)=[O:20])=[C:17]([F:22])[C:16]([CH2:23][NH:24][C:25](=[O:30])[C:26]([CH3:28])([CH3:27])[CH3:29])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 113598-AminoquinolineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid

Product 1

HCID 71677884HCID 71677884, compoundYield 10.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using quinolin-8-amine (Intermediate-48, 50 mg, 0.34 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 119 mg, 0.41 mmol), oxalyl chloride (78 mg, 0.62 mmol), DMF (1 drop) and DIPEA (132 mg, 1.02 mmol) in CH2Cl2 (5 mL) to afford 15 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.73 (s, 1H), 8.91 (s, 1H), 8.71 (d, J=8.1 Hz, 1H), 8.48 (d, 1H), 8.16 (t, 1H), 7.78 (d, 1H), 7.67 (t, J=7.2 Hz, 2H), 7.40 (m, 2H), 4.32 (d, 2H), 1.14 (s, 9H); MS (m/z): 414.23 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-0317312218e54852bbb678e2ce87b1d2
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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