Trifluoroacetic acid → HCID 25057342, compound

HRID 2423136Notes

Reaction equation

HRID 2423136 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]4[CH2:23][N:22]([C:24](OC(C)(C)C)=O)[CH2:21][CH2:20][O:19][C:15]4=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)([C:33](F)(F)[F:34])=O.C(N(CC)CC)C.FCCI>C(Cl)Cl>[F:34][CH2:33][CH2:24][N:22]1[CH2:23][C:14]2=[C:13]3[C:18](=[CH:17][CH:16]=[C:15]2[O:19][CH2:20][CH2:21]1)[N:10]([S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:8])=[O:9])[CH:11]=[CH:12]3

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 69804Ethane, 1-fluoro-2-iodo-HCID 67240578HCID 67240578, compound2×

Product 1

HCID 25057342HCID 25057342, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate (Intermediate 17, 16 mg, 0.040 mmol) was dissolved in DCM (1 mL) and TFA (0.5 mL) was added. The reaction mixture was heated to reflux, and immediately allowed to cool to room temperature. The solution was evaporated and the residue was dissolved in DMF (0.5 mL). Triethylamine (0.011 mL, 0.080 mmol) was added and the reaction mixture was stirred for 5 minutes before 1-fluoro-2-iodoethane (0.063 mL, 0.080 mmol) was added. The solution was stirred at 60° C. overnight. The solution was evaporated and the crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN) to give the title compound (6.9 mg). MS m/z 375 [M+H]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customThe solution was evaporated
  4. dissolutionthe residue was dissolved in DMF (0.5 mL)
  5. additionwas added
  6. customThe solution was evaporated
  7. customthe crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN)

Sources & evidence

ORD record
ord-7b7f0a270b424a5598eee142ce88cf84
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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