Methyl 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylate → methyl cis-(3aRS,9bRS)-5-acetyl-7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate

HRID 927918Notes

Reaction equation

HRID 927918 reaction equation
[CH2:1]([N:3]([CH2:35][CH3:36])[CH2:4]/[CH:5]=[CH:6]\[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([NH:17][C:18]1[C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]2[C:21]([C:22]3[CH:34]=[CH:33][O:32][C:23]=3CO2)=[CH:20][CH:19]=1)(=[O:16])=[O:15])[CH3:2].[C:37]([N:40]1C2C(=CC=C(NS(C3C=CC(F)=CC=3Br)(=O)=O)C=2C(OC)=O)[C@H]2CCO[C@H]2[CH2:41]1)(=[O:39])[CH3:38]>>[C:37]([N:40]1[C:26]2[C:21](=[CH:20][CH:19]=[C:18]([NH:17][S:14]([C:8]3[CH:9]=[CH:10][C:11]([F:13])=[CH:12][C:7]=3/[CH:6]=[CH:5]\[CH2:4][N:3]([CH2:1][CH3:2])[CH2:35][CH3:36])(=[O:15])=[O:16])[C:27]=2[C:28]([O:30][CH3:31])=[O:29])[C@H:22]2[CH2:34][CH2:33][O:32][C@H:23]2[CH2:41]1)(=[O:39])[CH3:38]

Participants

3

Reactant 2

HCID 86684725Methyl 7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylateHCID 86713284methyl cis-(3aRS,9bRS)-5-acetyl-7-(2-bromo-4-fluorobenzenesulfonylamino)-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate2×

Product 1

HCID 86713243methyl cis-(3aRS,9bRS)-5-acetyl-7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate

Conditions

Temperature
80 °C

Procedure

Prepared by proceeding in a similar manner to Intermediate 9, starting from methyl cis-(3aRS,9bRS)-5-acetyl-7-(2-bromo-4-fluorobenzenesulfonylamino)-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate (Intermediate 28) and heating at 80° C. for 2 hours.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-7cbbb331a77447bf8979e94933f134ef
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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