Nitrogen → HCID 25070281, compound

HRID 1096500Notes

Reaction equation

HRID 1096500 reaction equation
[CH3:1][CH:2]1[C:13]2[C:14]3[C:6](=[CH:7][N:8]([S:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)(=[O:25])=[O:24])[C:9]=3[CH:10]=[CH:11][C:12]=2OS(C(F)(F)F)(=O)=O)[CH2:5][CH2:4][N:3]1C(OC(C)(C)C)=O.N#N.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][CH:2]1[C:13]2[C:14]3[C:6](=[CH:7][N:8]([S:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)(=[O:25])=[O:24])[C:9]=3[CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][NH:3]1

Participants

6

Reactant 3

HCID 947Nitrogen2×HCID 2723923Ammonium formateHCID 59848829HCID 59848829, compound

Product 1

HCID 25070281HCID 25070281, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 6-methyl-1-(phenylsulfonyl)-7-{[(trifluoromethyl)sulfonyl]oxy}-1,3,4,6-tetrahydro-5H-azepino[5,4,3-cd]indole-5-carboxylate, Intermediate 16 (16 mg, 0.028 mmol) in MeOH (4 mL) and was carefully added to a 16 mm test tube containing Pd/C (35 mg). The suspension was purged with N2, ammonium formate (88 mg, 1.4 mmol) was added in one portion, the mixture was N2-purged once more and the mixture was stirred at room temperature over two days. The detriflated intermediate was purified with preparative HPLC (ACE C8 5 mm, water containing 0.1% TFA —CH3CN). The pure fraction was evaporated at reduced pressure, DCM/TFA 50/50, (1 mL) was added and the mixture was left at room temperature for one hour. The crude was purified by preparative HPLC (Xterra C18, 10 mM NH4CO3 (pH 10)-CH3CN) to give 0.8 mg of the title compound as a white oil. MS (ESI) m/z 326 [M+H]+.

Workup

  1. additionwas added in one portion
  2. custompurged once more
  3. customThe detriflated intermediate was purified with preparative HPLC (ACE C8 5 mm, water containing 0.1% TFA —CH3CN)
  4. customThe pure fraction was evaporated at reduced pressure, DCM/TFA 50/50, (1 mL)
  5. additionwas added
  6. waitthe mixture was left at room temperature for one hour
  7. customThe crude was purified by preparative HPLC (Xterra C18, 10 mM NH4CO3 (pH 10)-CH3CN)

Sources & evidence

ORD record
ord-29ee98e077cd40a2813830d999e836ad
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

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