Trifluoroacetic acid → HCID 68769883, compound

HRID 1174531Notes

Reaction equation

HRID 1174531 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Br:26])[CH:24]=3)[N:19]([S:27]([C:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:33]([O:40][CH3:41])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH:18]=2)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45]>ClCCl>[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45].[Br:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[N:19]([S:27]([C:30]1[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33]([O:40][CH3:41])=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH:18]=[C:17]2[C:15]([N:11]1[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1)=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68772447HCID 68772447, compound

Product 1

HCID 68769883HCID 68769883, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[5-Bromo-1-(4-methoxy-naphthalene-1-sulfonyl)-1H-indole-3-carbonyl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester (A) (45 mg, 0.07 mmol) in dichloromethane (5 cm3) was added trifluoroacetic acid (2 cm3). The solution was shaken at room temperature for 1 h before the solvent was removed under reduced pressure. The residue was dissolved in N,N-dimethylformamide (DMF) (1 cm3) and purified using reverse phase HPLC (Agilent Technologies, CombiHT SB-C18, Preparative cartridge 21.2×100 mm, 5-micron) using a linear gradient of water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid). The desired peak was then evaporated under reduced pressure to afford the title compound (83) (45.9 mg, 27%). Positive ion APCI (M+H)+ 543.4.

Workup

  1. customwas removed under reduced pressure
  2. dissolutionThe residue was dissolved in N,N-dimethylformamide (DMF) (1 cm3)
  3. custompurified
  4. customThe desired peak was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-c85208031c344cf89d019542ceda8135
Source dataset
uspto-grants-2010_11
Patent number
US07838518B2

Reaction notes

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