Piperazine → HCID 53346363, compound

HRID 1095799Notes

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[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>>[Cl:27][C:26]1[CH:25]=[N:24][CH:23]=[C:22]([Cl:28])[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:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[C:10]([O:29][CH3:30])=[CH:11][CH:12]=2)[NH:17][C:16](=[O:19])[CH:15]=1

Participants

Reactant 2

HCID 4837Piperazine

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

Product 1

HCID 53346363HCID 53346363, 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 piperazine following the procedure outlined in Example 15 (modifications: 40° C., 8 h, purified by reverse-phase HPLC). 1H NMR (400 MHz, DMSO-d6, bis HCl salt): δ 11.79 (br, 1H), 10.51 (s, 1H), 9.81 (br, 1H), 9.73 (br, 1H), 9.25 (s, 1H), 8.82 (s, 2H), 8.02 (d, 1H), 7.17 (d, 1H), 4.97 (s, 1H), 4.01 (t, 2H), 3.95 (s, 3H), 3.68 (br d, 2H), 3.58-3.35 (br m, 4H), 3.26 (br, 2H), 3.13 (m, 2H), 1.84-1.70 (m, 4H), 1.50-1.32 (m, 4H); MS (ESI): 520.4.

Workup

customoutlined in Example 15 (modifications: 40° C., 8 h, purified by reverse-phase HPLC)

Sources & evidence

ORD record: ord-629ca174de4146ca9f86551ea2f9605b
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138205B2

Reaction notes

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