Hexahydro-1,4-diazepine → 8-(6-(1,4-Diazepan-1-yl)hexyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one

HRID 1095802Notes

Reaction equation

HRID 1095802 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].[NH:31]1[CH2:37][CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>>[N:31]1([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]2[C:10]([O:29][CH3:30])=[CH:11][CH:12]=[C:13]3[C:18]=2[NH:17][C:16](=[O:19])[CH:15]=[C:14]3[NH:20][C:21]2[C:22]([Cl:28])=[CH:23][N:24]=[CH:25][C:26]=2[Cl:27])[CH2:37][CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1

Participants

3

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 592681178-(6-chlorohexyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one2×

Product 1

HCID 533464708-(6-(1,4-Diazepan-1-yl)hexyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxyquinolin-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 1,4-diazepane following the procedure outlined in Example 18, Step 2 (modifications: 40° C., 8 h). 1H NMR (400 MHz, DMSO-d6): δ 8.68 (s, 2H), 7.85 (d, 1H), 7.00 (d, 1H), 4.69 (s, 1H), 3.95 (t, 2H), 3.88 (s, 3H), 2.79 (t, 2H), 2.74 (m, 2H), 2.60-2.52 (m, 4H), 2.40 (t, 2H), 1.74 (m, 2H), 1.63 (m, 2H), 1.39 (m, 4H), 1.30 (m, 2H) [NH's not seen]; MS (ESI): 534.3.

Workup

  1. customoutlined in Example 18, Step 2 (modifications: 40° C., 8 h)

Sources & evidence

ORD record
ord-942141859e6a4f699148c474582ac24d
Source dataset
uspto-grants-2012_03
Patent number
US08138205B2

Reaction notes

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