Water → HCID 57559128, compound

HRID 1094603Notes

Reaction equation

HRID 1094603 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:11]=2[CH:10](O)[CH2:9][N:8]([C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH:7]=1)=[O:5])[CH3:2].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH2:45]([SH:47])[CH3:46].O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:11]=2[CH:10]([S:47][CH2:45][CH3:46])[CH2:9][N:8]([C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 67749Trifluoromethanesulfonic anhydrideHCID 57559135HCID 57559135, compound

Product 1

HCID 57559128HCID 57559128, compoundYield 1.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(4-fluorobenzoyl)-1-hydroxy-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester (60 mg, 0.3 mmol) in DCM (2 mL) was added trifluoromethanesulfonic anhydride (50 mL, 0.6 mmol) at 0° C. and the mixture was stirred for 1 hour at 0° C. Ethanethiol (34 mL, 0.9 mmol) was added and the reaction mixture was stirred overnight at 20° C. Water was added and organic layer was separated. The aqueous layer was extracted with DCM. The combined organic layer was then washed with water and dried over MgSO4. Evaporation of solvent gave a crude product, which was purified by column chromatography on silica gel, eluted with MeOH-DCM (1:19) to give the title compound (2 mg); 1NMR (CDCl3): δ 8.59 (1H, s), 8.77 (1H, d), 7.54 (2H, m), 7.36 (1H, ), 7.19 (1H, m), 7.06 (2H, m), 6.73 (1H, s), 4.41 (2H, m), 4.21-4.30 (3H, m), 2.59-2.69 (2H, m), 1.28 (3H, t), 1.19 (3H, t). MS (ES): 439 (MH+).

Workup

  1. stirringthe reaction mixture was stirred overnight at 20° C
  2. customorganic layer was separated
  3. extractionThe aqueous layer was extracted with DCM
  4. washThe combined organic layer was then washed with water
  5. dry with materialdried over MgSO4
  6. customEvaporation of solvent
  7. customgave a crude product, which
  8. customwas purified by column chromatography on silica gel
  9. washeluted with MeOH-DCM (1:19)

Sources & evidence

ORD record
ord-a302da9511a24155b5df95de67b4a0e9
Source dataset
uspto-grants-2012_03
Patent number
US08133992B2

Reaction notes

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