5-Ethyl-5-hydroxy-1,4,5,8-tetrahydrooxepino[3,4-c]pyridine-3,9-dione → 5,12-diethyl-9-fluoro-5-hydroxy-10-methoxy-1,4,5,13-tetrahydro-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione

HRID 720498Notes

Reaction equation

HRID 720498 reaction equation
Cl[C:2]1[C:11]([CH2:12]O)=[C:10]([CH2:14][CH3:15])[C:9]2[C:4](=[CH:5][C:6]([F:18])=[C:7]([O:16][CH3:17])[CH:8]=2)[N:3]=1.[CH2:19]([C:21]1([OH:34])[C:31]2[CH:30]=[CH:29][NH:28][C:27](=[O:32])[C:26]=2[CH2:25][O:24][C:23](=[O:33])[CH2:22]1)[CH3:20]>>[CH2:19]([C:21]1([OH:34])[C:31]2[CH:30]=[C:29]3[N:28]([CH2:12][C:11]4[C:2]3=[N:3][C:4]3[CH:5]=[C:6]([F:18])[C:7]([O:16][CH3:17])=[CH:8][C:9]=3[C:10]=4[CH2:14][CH3:15])[C:27](=[O:32])[C:26]=2[CH2:25][O:24][C:23](=[O:33])[CH2:22]1)[CH3:20]

Participants

3

Reactant 2

HCID 105370475-Ethyl-5-hydroxy-1,4,5,8-tetrahydrooxepino[3,4-c]pyridine-3,9-dioneHCID 21891951HCID 21891951, compound

Product 1

HCID 218918945,12-diethyl-9-fluoro-5-hydroxy-10-methoxy-1,4,5,13-tetrahydro-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione

Procedure

(2-chloro-4-ethyl-7-fluoro-6-methoxy-3-quinolinyl)methanol is coupled with compound (M) as described in Stage 11.j. of Example 11. The resultant coupled product is cyclized according to the procedure described in Stage 11.k. A yellow solid is obtained, m.p.>275° C.

Workup

  1. customA yellow solid is obtained

Sources & evidence

ORD record
ord-c94e3d94cfc241a7968c661b4b5ffa0b
Source dataset
uspto-grants-2006_11
Patent number
US07135478B2

Reaction notes

Loading…