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

HRID 20675

Reaction equation

HRID 20675 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][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][CH2:8][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]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 8083MorpholineHCID 248495698-(5-Bromopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

Product 1

HCID 248497594-(3,5-Dichloropyridin-4-ylamino)-7-methoxy-8-(5-morpholinopentyloxy)-2H-chromen-2-one

Procedure

The title compound was prepared from morpholine and 8-(5-bromopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one (Example 28) following the procedure outlined in Example 52. 1H NMR (400 MHz, DMSO-d6): δ 9.52 (br s, 1H), 8.80 (s, 2H), 7.94 (d, 1H), 7.19 (d, 1H), 4.62 (s, 1H), 3.98 (t, 2H), 3.91 (s, 3H), 3.55 (br, 4H), 2.51-2.15 (br, 6H), 1.69 (m, 2H), 1.47 (m, 4H); MS (ESI): 507.9.

Sources & evidence

ORD record
ord-be6f8f891af645c9ab74ed3729670458
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Linked notes

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