1-Methylpiperazine → 4-(3,5-Dichloropyridin-4-ylamino)-7-methoxy-8-(4-(4-methylpiperazin-1-yl)butoxy)-2H-chromen-2-one

HRID 20689Notes

Reaction equation

HRID 20689 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[C:15]([O:34][CH3:35])=[CH:16][CH:17]=[C:18]2[C:23]=1[O:22][C:21](=[O:24])[CH:20]=[C:19]2[NH:25][C:26]1[C:31]([Cl:32])=[CH:30][N:29]=[CH:28][C:27]=1[Cl:33]>>[Cl:33][C:27]1[CH:28]=[N:29][CH:30]=[C:31]([Cl:32])[C:26]=1[NH:25][C:19]1[C:18]2[C:23](=[C:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[C:15]([O:34][CH3:35])=[CH:16][CH:17]=2)[O:22][C:21](=[O:24])[CH:20]=1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 248495678-(4-bromobutoxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

Product 1

HCID 248498884-(3,5-Dichloropyridin-4-ylamino)-7-methoxy-8-(4-(4-methylpiperazin-1-yl)butoxy)-2H-chromen-2-one

Procedure

The title compound was prepared from 1-methylpiperazine and 8-(4-bromobutoxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one (Example 25) following the procedure outlined in Example 52. 1H NMR (400 MHz, DMSO-d6; bis HCl salt): δ 11.74 (br, 2H), 9.66 (s, 1H), 8.82 (s, 2H), 8.02 (d, 1H), 7.22 (d, 1H), 4.63 (s, 1H), 4.01 (t, 2H), 3.94 (s, 3H), 3.84-3.18 (br m, 10H), 2.81 (s, 3H), 1.97 (m, 2H), 1.75 (m, 2H); MS (ESI): 507.0.

Sources & evidence

ORD record
ord-fb44e24b1aa94723b6b7febd270bf0a9
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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