Morpholine → 4-(3,5-Dichloropyridin-4-ylamino)-7-methoxy-8-(4-morpholinobutoxy)-2H-chromen-2-one

HRID 20690Notes

Reaction equation

HRID 20690 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:14]([O:33][CH3:34])=[CH:15][CH:16]=[C:17]2[C:22]=1[O:21][C:20](=[O:23])[CH:19]=[C:18]2[NH:24][C:25]1[C:30]([Cl:31])=[CH:29][N:28]=[CH:27][C:26]=1[Cl:32]>>[Cl:32][C:26]1[CH:27]=[N:28][CH:29]=[C:30]([Cl:31])[C:25]=1[NH:24][C:18]1[C:17]2[C:22](=[C:13]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[C:14]([O:33][CH3:34])=[CH:15][CH:16]=2)[O:21][C:20](=[O:23])[CH:19]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 248495678-(4-bromobutoxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

Product 1

HCID 248498894-(3,5-Dichloropyridin-4-ylamino)-7-methoxy-8-(4-morpholinobutoxy)-2H-chromen-2-one

Procedure

The title compound was prepared from morpholine 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; HCl salt): δ 10.67 (br, 1H), 9.65 (br s, 1H), 8.82 (s, 2H), 8.01 (d, 1H), 7.22 (d, 1H), 4.64 (s, 1H), 4.01 (t, 2H), 3.93 (s, 3H), 3.92 (m, 2H), 3.76 (t, 2H), 3.42 (d, 2H), 3.20 (m, 2H), 3.05 (m, 2H), 1.97 (m, 2H), 1.74 (m, 2H); MS (ESI): 494.0.

Sources & evidence

ORD record
ord-5463a61500a24191adb453f447212d07
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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