1-(6-Bromo-4-chloroquinolin-3-yl)propan-1-one → HCID 178458756, compound

HRID 2271533Notes

Reaction equation

HRID 2271533 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:15])[CH2:13][CH3:14])=[C:5]2Cl.Cl.Cl.[CH3:19][N:20]([CH3:28])[C@H:21]1[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:15])[CH2:13][CH3:14])=[C:5]2[NH:27][C@H:24]1[CH2:25][CH2:26][C@H:21]([N:20]([CH3:28])[CH3:19])[CH2:22][CH2:23]1

Participants

3

Reactant 2

HCID 866928451-(6-Bromo-4-chloroquinolin-3-yl)propan-1-oneHCID 178484109HCID 178484109, compound

Product 1

HCID 178458756HCID 178458756, compoundYield 58%

Procedure

Following general procedure C, 1-(6-bromo-4-chloroquinolin-3-yl)propan-1-one (800 mg, 2.68 mmol) was reacted with trans-N1,N1-dimethylcyclohexane-1,4-diamine dihydrochloride (692 mg, 3.21 mmol) to afford the desired product (629 mg, 58%) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 10.77 (br d, J=8.1 Hz, 1H), 9.01 (s, 1H), 8.27 (d, J=2.0 Hz, 1H), 7.84-7.68 (m, 2H), 4.05-3.89 (m, 1H), 3.08 (q, J=7.2 Hz, 2H), 2.33 (s, 6H), 2.33-2.23 (m, 2H), 2.12-1.99 (m, 2H), 1.63-1.31 (m, 4H), 1.25 (t, J=7.2 Hz, 3H).

Sources & evidence

ORD record
ord-3c7b9272d02e42259aa2463222210425
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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