Morpholine → HCID 66685688, compound

HRID 1778375Notes

Reaction equation

HRID 1778375 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].C(N(C(C)C)CC)(C)C.[NH:55]1[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1>C(Cl)Cl>[F:41][C:38]1[CH:39]=[CH:40][C:35]([S:32]([N:23]([C:11]2[C:10]([C:8]([O:7][CH3:6])=[O:9])=[C:19]3[C:14]([C:15]4[CH:22]=[CH:21][O:20][C:16]=4[CH2:17][O:18]3)=[CH:13][CH:12]=2)[CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:29])[CH3:30])(=[O:33])=[O:34])=[C:36](/[CH:42]=[CH:43]\[CH2:44][N:55]2[CH2:60][CH2:59][O:58][CH2:57][CH2:56]2)[CH:37]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66693986HCID 66693986, compound2×

Product 1

HCID 66685688HCID 66685688, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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, 1.57 g) and diisopropylethylamine (0.859 g) in DCM (25 mL) and the mixture was stirred in an ice bath for 20 minutes. Morpholine (0.689 g) was added and the reaction mixture was stirred at room temperature for 90 minutes. It was washed with water, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 10-80% to give methyl 7-{N-[4-fluoro-2((Z)-3-{morpholin-4-yl}prop-1-enyl)benzenesulfonyl]-N-(2-trimethylsilanylethoxy-methyl)amino}-4H-furo[2,3-c]chromene-6-carboxylate (1.15 g) as a yellow gum.

Workup

  1. temperaturecooled
  2. stirringthe reaction mixture was stirred at room temperature for 90 minutes
  3. washIt was washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 10-80%

Sources & evidence

ORD record
ord-8a6c88b5ee18418980ea79332450a404
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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