Diethanolamine → 8-(6-(Bis(2-hydroxyethyl)amino)hexyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one

HRID 1095808Notes

Reaction equation

HRID 1095808 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]([CH2:35][CH2:36][OH:37])[CH2:32][CH2:33][OH:34]>>[OH:34][CH2:33][CH2:32][N:31]([CH2:35][CH2:36][OH:37])[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]

Participants

3

Reactant 2

HCID 8113DiethanolamineHCID 592681178-(6-chlorohexyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one2×

Product 1

HCID 533447208-(6-(Bis(2-hydroxyethyl)amino)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 diethanolamine following the procedure outlined in Example 18, Step 2 (modifications: 40° C., 24 h then 60° C., 24 h). 1H NMR (400 MHz, DMSO-d6): δ 9.95 (s, 1H), 8.83 (s, 1H), 8.76 (s, 2H), 7.87 (d, 1H), 7.04 (d, 1H), 4.77 (s, 1H), 4.30 (br, 2H), 3.95 (t, 2H), 3.90 (s, 3H), 3.39 (m, 4H), 2.56-2.36 (m, 6H), 1.74 (m, 2H), 1.38 (m, 4H), 1.28 (m, 2H); MS (ESI): 539.3.

Workup

  1. custom40° C., 24 h
  2. custom60° C., 24 h

Sources & evidence

ORD record
ord-f3b35ac452f84c89afc79baf2db245f8
Source dataset
uspto-grants-2012_03
Patent number
US08138205B2

Reaction notes

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