1-Methylpiperazine → HCID 53346361, compound

HRID 1095797Notes

Reaction equation

HRID 1095797 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.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]Br.[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.ClCCCCCCOC1C(OC)=CC=C2C=1NC(=O)C=C2NC1C(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][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][N:37]3[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]3)[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[NH:12][C:11](=[O:22])[CH:10]=1

Participants

5

Reactant 4

HCID 531671-MethylpiperazineHCID 783091,7-DibromoheptaneHCID 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 53346361HCID 53346361, compound

Procedure

The title compound was prepared from 4-(3,5-dichloropyridin-4-ylamino)-8-hydroxy-7-methoxyquinolin-2(1H)-one (Intermediate 3), 1,7-dibromoheptane, and 1-methylpiperazine following the procedures outlined for Intermediate 4 (modifications: NMP (N-methylpyrrolidone) 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 11.87 (br, 2H), 10.46 (s, 1H), 9.22 (s, 1H), 8.81 (s, 2H), 8.01 (d, 1H), 7.16 (d, 1H), 4.95 (s, 1H), 4.01 (t, 2H), 3.94 (s, 3H), 3.84-3.20 (br m, 8H), 3.11 (m, 2H), 2.82 (s, 3H), 1.84-1.68 (m, 4H), 1.48-1.30 (m, 6H); MS (ESI): 548.3.

Sources & evidence

ORD record
ord-29ace1abf5724cba93b9deadebff1536
Source dataset
uspto-grants-2012_03
Patent number
US08138205B2

Reaction notes

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