Ethanol → HCID 70168826, compound

HRID 1426931Notes

Reaction equation

HRID 1426931 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:24](=[O:25])[N:22]([CH:23]=1)[CH2:21][C@@H:20](O)[CH2:19][NH:18][C:17](=[O:27])[C:16]1=[C:28]3[N:29]=[C:10]([CH:11]=[CH:12][N:13]3[N:14]=[CH:15]1)[N:9]1[C@@H:5]2[CH2:6][CH2:7][CH2:8]1.COCCN(S(F)(F)[F:40])CCOC.C(O)C.C([O-])(O)=O.[Na+]>CS(C)=O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:24](=[O:25])[N:22]([CH:23]=1)[CH2:21][C@H:20]([F:40])[CH2:19][NH:18][C:17](=[O:27])[C:16]1=[C:28]3[N:29]=[C:10]([CH:11]=[CH:12][N:13]3[N:14]=[CH:15]1)[N:9]1[C@@H:5]2[CH2:6][CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 70169989HCID 70169989, compound

Product 1

HCID 70168826HCID 70168826, compoundYield 12.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of (6R,13S)-9-fluoro-13-hydroxy-2,11,15,19,20,23-hexaazapentacyclo-[15.5.2.17,11.02,6.020,24]pentacosa-1(23),7,9,17(24),18,21-hexaene-16,25-dione (Example 5; 10 mg, 0.0251 mmol) in a mixture solvent of DCM (0.3 mL) and 3 drops of DMSO was treated with bis(2-methoxyethyl)amino-sulfur trifluoride (7.87 μL, 0.0427 mmol) at 0° C., followed by addition of a DCM (0.1 mL) solution of ethanol (0.231 mg, 0.00502 mmol), and the mixture was stirred at ambient temperature overnight. The reaction mixture was poured into saturated NaHCO3 and extracted with DCM, then dried (Na2SO4), filtered, and concentrated. The crude material was purified by reverse phase column chromatography (Biotage SP4 system C18 12+M cartridge, acetonitrile/water 5 to 50%) to give the title product as beige solid (1.3 mg, 12% yield). MS (apci) m/z=401.2 (M+H).

Workup

  1. extractionextracted with DCM
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by reverse phase column chromatography (Biotage SP4 system C18 12+M cartridge, acetonitrile/water 5 to 50%)

Sources & evidence

ORD record
ord-71cdd62b0db7478b907db02b57c87967
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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