Trifluoroacetic acid methylene chloride → HCID 25073118, compound

HRID 1096496Notes

Reaction equation

HRID 1096496 reaction equation
C(Cl)Cl.C(O)(C(F)(F)F)=O.[OH:11][C:12]1[CH:20]=[CH:19][C:18]2[N:17]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[CH:16]=[C:15]3[CH2:30][CH2:31][N:32](C(OC(C)(C)C)=O)[CH:33]([CH3:34])[C:13]=1[C:14]=23>>[CH3:34][CH:33]1[C:13]2=[C:14]3[C:18](=[CH:19][CH:20]=[C:12]2[OH:11])[N:17]([S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH:16]=[C:15]3[CH2:30][CH2:31][NH:32]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 59848833HCID 59848833, compound

Product 1

HCID 25073118HCID 25073118, compound

Procedure

A 50/50 mixture of DCM/TFA (1 mL) was added to tert-butyl 7-hydroxy-6-methyl-1-(phenylsulfonyl)-1,3,4,6-tetrahydro-5H-azepino[5,4,3-cd]indole-5-carboxylate, Intermediate 15 (16 mg, 0.036 mmol) and the mixture was stirred at room temperature for one hour. The solvent was evaporated at reduced pressure and the crude product was purified by preparative HPLC (Xterra C18, 10 mM NH4CO3 (pH 10)-CH3CN) to give 6.9 mg of the title compound. MS m/z 343 [M+H]+.

Workup

  1. customThe solvent was evaporated at reduced pressure
  2. customthe crude product was purified by preparative HPLC (Xterra C18, 10 mM NH4CO3 (pH 10)-CH3CN)

Sources & evidence

ORD record
ord-e7c32de90a2041c6bab5882509d68be9
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

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