4-(3,5-dichloropyridin-4-ylamino)-8-hydroxy-7-methoxy-2H-chromen-2-one → 4-(3,5-Dichloropyridin-4-ylamino)-8-(((3aS,4S,6aS)-2,2-dimethyl-6-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)-7-methoxy-2H-chromen-2-one

HRID 20672Notes

Reaction equation

HRID 20672 reaction equation
Br[CH2:2][C@H:3]1[C@@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@@H:6]2[C:5](=[O:13])[O:4]1.[Cl:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([Cl:36])[C:20]=1[NH:21][C:22]1[C:31]2[C:26](=[C:27]([OH:34])[C:28]([O:32][CH3:33])=[CH:29][CH:30]=2)[O:25][C:24](=[O:35])[CH:23]=1>>[Cl:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([Cl:36])[C:20]=1[NH:21][C:22]1[C:31]2[C:26](=[C:27]([O:34][CH2:2][C@H:3]3[C@H:7]4[C@H:6]([O:10][C:9]([CH3:12])([CH3:11])[O:8]4)[C:5](=[O:13])[O:4]3)[C:28]([O:32][CH3:33])=[CH:29][CH:30]=2)[O:25][C:24](=[O:35])[CH:23]=1

Participants

3

Reactant 2

HCID 248495704-(3,5-dichloropyridin-4-ylamino)-8-hydroxy-7-methoxy-2H-chromen-2-oneHCID 68741369(3aS,6R,6aR)-6-(bromomethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4-(3aH)-one

Product 1

HCID 248497564-(3,5-Dichloropyridin-4-ylamino)-8-(((3aS,4S,6aS)-2,2-dimethyl-6-oxotetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)-7-methoxy-2H-chromen-2-one

Procedure

The title compound was prepared from (3aS,6R,6aR)-6-(bromomethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4-(3aH)-one and 4-(3,5-dichloropyridin-4-ylamino)-8-hydroxy-7-methoxy-2H-chromen-2-one (Example 29) following the procedure outlined in Example 25. 1H NMR (400 MHz, DMSO-d6): δ 9.57 (s, 1H), 8.83 (s, 2H), 7.98 (d, 1H), 7.23 (s, 1H), 5.16 (m, 2H), 4.87 (m, 1H), 4.67 (s, 1H) 4.36 (m, 2H), 3.93 (s, 3H), 1.40 (s, 3H), 1.37 (s, 3H); MS (ESI): 522.8.

Sources & evidence

ORD record
ord-e93f368e53dd4e858db07cd7df9a85d3
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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