Triethylamine → cis-(3aRS,9bRS)-7-[2-(4-dimethylaminobutylamino)-benzenesulfonylamino]-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylic acid

HRID 927856Notes

Reaction equation

HRID 927856 reaction equation
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].C(N(CC)CC)C.F[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([NH:26][C:27]1[C:36]([C:37]([OH:39])=[O:38])=[C:35]2[C:30]([C@H:31]3[CH2:42][CH2:41][O:40][C@H:32]3[CH2:33][O:34]2)=[CH:29][CH:28]=1)(=[O:25])=[O:24]>C(#N)C.O>[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([NH:26][C:27]1[C:36]([C:37]([OH:39])=[O:38])=[C:35]2[C:30]([C@H:31]3[CH2:42][CH2:41][O:40][C@H:32]3[CH2:33][O:34]2)=[CH:29][CH:28]=1)(=[O:25])=[O:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 770634-DimethylaminobutylamineHCID 86713246cis-(3aRS,9bRS)-7-(2-fluorobenzenesulfonylamino)-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylic acid2×

Product 1

HCID 86713245cis-(3aRS,9bRS)-7-[2-(4-dimethylaminobutylamino)-benzenesulfonylamino]-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylic acidYield 33.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

4-Dimethylaminobutylamine (0.348 g) and triethylamine (0.2 ml) were added to a suspension of cis-(3aRS,9bRS)-7-(2-fluorobenzenesulfonylamino)-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylic acid (Intermediate 57, 0.15 g) in acetonitrile (1.5 mL) and the mixture was heated at 130° C. in a sealed tube for 36 hours. The mixture was then diluted with water (2 mL) and the solution was purified by preparative HPLC (C6-phenyl) eluting with a mixture of methanol and water, containing 0.1% formic acid, with a gradient of 5-98%. The isolated product was further purified by chromatography on silica eluting with a mixture of methanol and DCM with a gradient of 0-15% to give cis-(3aRS,9bRS)-7-[2-(4-dimethylaminobutylamino)-benzenesulfonylamino]-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylic acid (0.062 g) as a glass foam.

Workup

  1. customthe solution was purified by preparative HPLC (C6-phenyl)
  2. washeluting with a mixture of methanol and water
  3. additioncontaining 0.1% formic acid
  4. customThe isolated product was further purified by chromatography on silica eluting with a mixture of methanol and DCM with a gradient of 0-15%

Sources & evidence

ORD record
ord-877a6739a3eb4023824be3ae1cee6254
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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