(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone → HCID 178484093, compound

HRID 2271581Notes

Reaction equation

HRID 2271581 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]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2Cl.[CH3:18][N:19]([CH3:27])[C@H:20]1[CH2:25][CH2:24][C@H:23]([NH2:26])[CH2:22][CH2:21]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]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[NH:26][C@H:23]1[CH2:24][CH2:25][C@H:20]([N:19]([CH3:27])[CH3:18])[CH2:21][CH2:22]1

Participants

3

Reactant 2

HCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanoneHCID 178484105HCID 178484105, compound

Product 1

HCID 178484093HCID 178484093, compoundYield 36%

Procedure

Following general procedure B, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (870 mg, 2.80 mmol) was reacted with trans-N1,N1-dimethylcyclohexane-1,4-diamine (400 mg, 2.80 mmol) to afford the desired product (398 mg, 36%) as a light yellow solid: 1H NMR (300 MHz, CD3OD) δ 9.12 (s, 1H), 8.41 (d, J=2.0 Hz, 1H), 7.85 (dd, J=8.9, 2.0 Hz, 1H), 7.76 (d, J=8.9 Hz, 1H), 4.10-3.84 (m, 1H), 2.93-2.70 (m, 1H), 2.56-2.40 (m, 1H), 2.37 (s, 6H), 2.25 (d, J=12.0 Hz, 2H), 2.05 (d, J=11.4 Hz, 2H), 1.62-1.31 (m, 4H), 1.31-1.01 (m, 4H).

Sources & evidence

ORD record
ord-c1c1a72ea67744e3984cea0732259d04
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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