(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone → HCID 178483663, compound

HRID 2271584Notes

Reaction equation

HRID 2271584 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]([CH2:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([NH2:28])[CH2:24][CH2:23]1)[CH3:20]>>[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:28][C@H:25]1[CH2:26][CH2:27][C@H:22]([CH2:21][N:19]([CH3:20])[CH3:18])[CH2:23][CH2:24]1

Participants

3

Reactant 2

HCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanoneHCID 178483674HCID 178483674, compound

Product 1

HCID 178483663HCID 178483663, compoundYield 43.2%

Procedure

Following general procedure C, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (560 mg, 1.80 mmol) was reacted with trans-4-[(dimethylamino)methyl]cyclohexanamine (620 mg, 2.70 mmol) to afford the desired product (335 mg, 43%) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ 9.12 (s, 1H), 8.41 (d, J=2.0 Hz, 1H), 7.84 (dd, J=8.9, 2.1 Hz, 1H), 7.75 (d, J=8.9 Hz, 1H), 4.12-3.84 (m, 1H), 2.91-2.72 (m, 1H), 2.42-2.26 (m, J=6.6 Hz, 8H), 2.21 (d, J=11.6 Hz, 2H), 1.94 (d, J=12.1 Hz, 2H), 1.75-1.59 (m, 1H), 1.59-1.35 (m, 2H), 1.25-0.98 (m, 6H).

Sources & evidence

ORD record
ord-c3d6b175c40f465280cdc9dd613df438
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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