1-Methylhomopiperazine → 4-(3,5-Dichloropyridin-4-ylamino)-7-methoxy-8-(6-(4-methyl-1,4-diazepan-1-yl)hexyloxy)quinolin-2(1H)-one

HRID 1095803Notes

Reaction equation

HRID 1095803 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[C:10]([O:29][CH3:30])=[CH:11][CH:12]=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[C:14]2[NH:20][C:21]1[C:26]([Cl:27])=[CH:25][N:24]=[CH:23][C:22]=1[Cl:28].[CH3:31][N:32]1[CH2:38][CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>>[Cl:28][C:22]1[CH:23]=[N:24][CH:25]=[C:26]([Cl:27])[C:21]=1[NH:20][C:14]1[C:13]2[C:18](=[C:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:35]3[CH2:36][CH2:37][CH2:38][N:32]([CH3:31])[CH2:33][CH2:34]3)[C:10]([O:29][CH3:30])=[CH:11][CH:12]=2)[NH:17][C:16](=[O:19])[CH:15]=1

Participants

3

Reactant 2

HCID 2283491-MethylhomopiperazineHCID 592681178-(6-chlorohexyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one2×

Product 1

HCID 533464714-(3,5-Dichloropyridin-4-ylamino)-7-methoxy-8-(6-(4-methyl-1,4-diazepan-1-yl)hexyloxy)quinolin-2(1H)-one

Procedure

The title compound was prepared from 8-(6-chlorohexyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one (Intermediate 4) and 1-methyl-1,4-diazepane following the procedure outlined in Example 18, Step 2 (modifications: 40° C., 24 h). 1H NMR (400 MHz, DMSO-d6): δ 9.93 (s, 1H), 8.82 (br, 1H), 8.75 (s, 2H), 7.87 (d, 1H), 7.04 (d, 1H), 4.76 (s, 1H), 3.95 (t, 2H), 3.89 (s, 3H), 2.62-2.42 (m, 8H), 2.37 (t, 2H), 2.21 (s, 3H), 1.74 (m, 2H), 1.66 (m, 2H), 1.38 (m, 4H), 1.29 (m, 2H); MS (ESI): 548.3.

Workup

  1. customoutlined in Example 18, Step 2 (modifications: 40° C., 24 h)

Sources & evidence

ORD record
ord-72f1c7a3c5a242449a08fa14a55521da
Source dataset
uspto-grants-2012_03
Patent number
US08138205B2

Reaction notes

Loading…