Water → HCID 178480559, compound

HRID 1670650Notes

Reaction equation

HRID 1670650 reaction equation
FC(F)(F)C(O)=[O:4].O.C(O)(=O)/C=C\C(O)=O.[F:17][C:18]1[CH:19]=[CH:20][C:21]2=[C:22]([CH:52]=1)[O:23][CH2:24][C:25]1[CH:51]=[CH:50][CH:49]=[CH:48][C:26]=1/[C:27]/2=[CH:28]\[C:29]1[CH:47]=[CH:46][C:32]2[N:33]([C@@H:39]3[C@@H:43]([OH:44])[CH2:42][N:41]([CH3:45])[CH2:40]3)/[C:34](=[N:36]/[C:37]#[N:38])/[NH:35][C:31]=2[CH:30]=1.[OH-].[Na+]>C(OCC)(=O)C>[F:17][C:18]1[CH:19]=[CH:20][C:21]2=[C:22]([CH:52]=1)[O:23][CH2:24][C:25]1[CH:51]=[CH:50][CH:49]=[CH:48][C:26]=1/[C:27]/2=[CH:28]\[C:29]1[CH:47]=[CH:46][C:32]2[N:33]([C@@H:39]3[C@@H:43]([OH:44])[CH2:42][N:41]([CH3:45])[CH2:40]3)/[C:34](=[N:36]/[C:37]([NH2:38])=[O:4])/[NH:35][C:31]=2[CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 178480558HCID 178480558, compound

Product 1

HCID 178480559HCID 178480559, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of trifluoroacetic acid (30 mL) and water (6.0 eq, 100 mmol, 1.81 mL) in an ice bath add (E)-N-(5-((E)-(3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)methyl)-1-((3S,4S)-4-hydroxy-1-methylpyrrolidin-3-yl)-1H-benzo[d]imidazol-2(3H)-ylidene)cyanamide maleate (16.73 mmol, 10.00 g). Allow the resulting suspension to warm up to room temperature and stir for 2 h. Dilute the solution with ethyl acetate (250 mL), cool the mixture in an ice bath for 30 min, and treat with 5 N sodium hydroxide to pH=11. Wash the organic layer with brine, dry over anhydrous sodium sulfate, and concentrate under reduced pressure. Purify the residue by column chromatography eluting with 2.5 to 5% methanol in ethyl acetate to obtain a white solid. Dry in a vacuum oven at 40° C. overnight to obtain the title compound (6.74 g, 81%). LC-MS m/z 500.2 [M+H]+.

Workup

  1. temperaturecool the mixture in an ice bath for 30 min
  2. washWash the organic layer with brine
  3. dry with materialdry over anhydrous sodium sulfate
  4. concentrationconcentrate under reduced pressure
  5. customPurify the residue by column chromatography
  6. washeluting with 2.5 to 5% methanol in ethyl acetate
  7. customto obtain a white solid
  8. customDry in a vacuum oven at 40° C. overnight

Sources & evidence

ORD record
ord-0ad6e90a5a3b4114a385c2a3f37ee32f
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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