(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone → HCID 178484040, compound

HRID 2271583Notes

Reaction equation

HRID 2271583 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.[NH2:18][CH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([N:26]([CH3:28])[CH3:27])[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:18][CH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([N:26]([CH3:28])[CH3:27])[CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanoneHCID 178484042HCID 178484042, compound

Product 1

HCID 178484040HCID 178484040, compoundYield 59.1%

Procedure

Following general procedure C, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (537 mg, 1.73 mmol) was reacted with trans-4-(aminomethyl)-N,N-dimethylcyclohexanamine (595 mg, 2.60 mmol) to afford the desired product (440 mg, 59%) as a white solid: 1H NMR (300 MHz, CH3OD) δ 9.13 (s, 1H), 8.48 (d, J=2.0 Hz, 1H), 7.83 (dd, J=9.0, 2.0 Hz, 1H), 7.73 (d, J=8.9 Hz, 1H), 3.65 (d, J=6.4 Hz, 2H), 2.91-2.67 (m, 1H), 2.41-2.18 (m, 7H), 1.99 (d, J=10.1 Hz, 4H), 1.67 (d, J=3.3 Hz, 1H), 1.43-0.99 (m, 8H).

Sources & evidence

ORD record
ord-91b7eb04cb8f45bd87041f9d6690a41d
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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