1,3-Propanediamine, N1,N1,N3-trimethyl- → HCID 53346472, compound

HRID 1095804Notes

Reaction equation

HRID 1095804 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]([CH3:38])[CH2:33][CH2:34][CH2:35][NH:36][CH3:37]>>[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:36]([CH2:35][CH2:34][CH2:33][N:32]([CH3:38])[CH3:31])[CH3:37])[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 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 592681178-(6-chlorohexyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one2×

Product 1

HCID 53346472HCID 53346472, compound

Procedure

The title compound was prepared from 8-(6-chlorohexyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one (Intermediate 4) and N1,N1,N3-trimethylpropane-1,3-diamine following the procedure outlined in Example 18, Step 2 (modifications: 40° C., 24 h then 60° C., 4 h). 1H NMR (400 MHz, DMSO-d6, bis HCl salt): δ 10.78-10.62 (br, 2H), 10.33 (s, 1H), 9.17 (s, 1H), 8.81 (s, 2H), 8.00 (d, 1H), 7.15 (d, 1H), 4.93 (s, 1H), 4.01 (t, 2H), 3.94 (s, 3H), 3.25-2.95 (m, 6H), 2.76-2.70 (m, 9H), 2.13 (m, 2H), 1.80 (m, 2H), 1.73 (m, 2H), 1.47 (m, 2H), 1.37 (m, 2H); MS (ESI): 550.5.

Workup

  1. custom40° C., 24 h
  2. custom60° C., 4 h

Sources & evidence

ORD record
ord-edf4ba90d8f24eabae7c7ad077c60aad
Source dataset
uspto-grants-2012_03
Patent number
US08138205B2

Reaction notes

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