Ethylamine → HCID 66692817, compound

HRID 1778371Notes

Reaction equation

HRID 1778371 reaction equation
CS(Cl)(=O)=O.[CH3:6][O:7][C:8]([C:10]1[C:11]([N:23]([S:32]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=2/[CH:42]=[CH:43]\[CH2:44]O)(=[O:34])=[O:33])[CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])=[CH:12][CH:13]=[C:14]2[C:19]=1[O:18][CH2:17][C:16]1[O:20][CH:21]=[CH:22][C:15]2=1)=[O:9].[CH:46]([N:49](C(C)C)CC)(C)[CH3:47].C(N)C>C(Cl)Cl>[CH2:46]([NH:49][CH2:44]/[CH:43]=[CH:42]\[C:36]1[CH:37]=[C:38]([F:41])[CH:39]=[CH:40][C:35]=1[S:32]([N:23]([C:11]1[C:10]([C:8]([O:7][CH3:6])=[O:9])=[C:19]2[C:14]([C:15]3[CH:22]=[CH:21][O:20][C:16]=3[CH2:17][O:18]2)=[CH:13][CH:12]=1)[CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])(=[O:33])=[O:34])[CH3:47]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66693986HCID 66693986, compound2×

Product 1

HCID 66692817HCID 66692817, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (0.100 g) was added to an ice-cooled, stirred solution of methyl-7-{N-[4-fluoro-2-((Z)-3-hydroxyprop-1-enyl)benzenesulfonyl]-N-(2-trimethylsilanylethoxymethyl)amino]-4H-furo[2,3-c]chromene-6-carboxylate (Intermediate 48, 0.413 g) and diisopropylethylamine (0.226 g) in DCM (7 mL). The reaction mixture was stirred with ice cooling for 30 minutes. Ethylamine (2M in THF, 2 mL) was added and the reaction mixture was stirred at room temperature for 5 hours. It was diluted with DCM and washed with water. The organic layer was dried (Na2SO4), filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica, eluting with DMAW 350, followed by DMAW 240 and then DMAW 120. The resultant product was azeotroped with toluene and ethanol to give methyl 7-{N-[2-((Z)-3-ethylaminoprop-1-enyl)-4-fluorobenzenesulfonyl]-N-(2-trimethylsilanylethoxymethyl)amino}-4H-furo[2,3-c]chromene-6-carboxylate (0.401 g) as a dark yellow gum.

Workup

  1. temperaturecooled
  2. stirringthe reaction mixture was stirred at room temperature for 5 hours
  3. washwashed with water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified by chromatography on silica
  8. washeluting with DMAW 350
  9. customThe resultant product was azeotroped with toluene and ethanol

Sources & evidence

ORD record
ord-c5fbe6ed4e3c4392962c5e675650fbd0
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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