1-Methylpiperazine → HCID 53346362, compound

HRID 1095798Notes

Reaction equation

HRID 1095798 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:23])[C:7]=1[NH:8][C:9]1[C:18]2[C:13](=[C:14]([OH:21])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[NH:12][C:11](=[O:22])[CH:10]=1.[CH3:24][N:25]1[CH2:30]CN[CH2:27][CH2:26]1.ClCCCCCCO[C:39]1[C:40](OC)=[CH:41][CH:42]=[C:43]2[C:48]=1[NH:47][C:46](=O)[CH:45]=[C:44]2NC1C(Cl)=CN=CC=1Cl>>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:23])[C:7]=1[NH:8][C:9]1[C:18]2[C:13](=[C:14]([O:21][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][N:47]3[CH2:48][CH2:24][N:25]([CH3:30])[CH2:26][CH2:27]3)[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[NH:12][C:11](=[O:22])[CH:10]=1

Participants

4

Reactant 3

HCID 531671-MethylpiperazineHCID 592681178-(6-chlorohexyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxyquinolin-2(1H)-oneHCID 592681184-(3,5-dichloropyridin-4-ylamino)-8-hydroxy-7-methoxyquinolin-2(1H)-one2×

Product 1

HCID 53346362HCID 53346362, compound

Procedure

The title compound was prepared from 4-(3,5-dichloropyridin-4-ylamino)-8-hydroxy-7-methoxyquinolin-2(1H)-one (Intermediate 3), 1,8-dibromoocttane, and 1-methylpiperazine following the procedures outlined for Intermediate 4 (modifications: NMP used as solvent and 5.0 equiv of dibromide used) and Example 18, Step 2. 1H NMR (400 MHz, DMSO-d6, bis HCl salt): δ 11.89 (br, 2H), 10.49 (s, 1H), 9.24 (s, 1H), 8.81 (s, 2H), 8.01 (d, 1H), 7.16 (d, 1H), 4.97 (s, 1H), 4.01 (t, 2H), 3.94 (s, 3H), 3.82-3.20 (br m, 8H), 3.10 (m, 2H), 2.81 (s, 3H), 1.84-1.66 (m, 4H), 1.46-1.26 (m, 8H); MS (ESI): 562.3.

Sources & evidence

ORD record
ord-f02ed4c80997436eb1d44e58132c1f59
Source dataset
uspto-grants-2012_03
Patent number
US08138205B2

Reaction notes

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