Trifluoroacetic acid → HCID 69832035, compound

HRID 1633797Notes

Reaction equation

HRID 1633797 reaction equation
[F:1][C:2]1[C:3]2[C:4]3[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]=3[C:12]([C:22]1[NH:23][CH:24]=[C:25]([CH3:28])[C:26]=1[CH3:27])=[CH:13][C:14]=2[S:15][CH2:16][CH2:17][NH:18]C(=O)O.C(OC(=O)NCCSC1C=C(C2NC=C(C)C=2C)C2C(=O)NC3C=2C=1C(F)=CC=3)(C)(C)C.[C:61]([OH:67])([C:63]([F:66])([F:65])[F:64])=[O:62].[OH-].[NH4+]>C(Cl)Cl.C(OCC)(=O)C>[F:64][C:63]([F:66])([F:65])[C:61]([OH:67])=[O:62].[NH2:18][CH2:17][CH2:16][S:15][C:14]1[CH:13]=[C:12]([C:22]2[NH:23][CH:24]=[C:25]([CH3:28])[C:26]=2[CH3:27])[C:5]2[C:6](=[O:11])[NH:7][C:8]3[C:4]=2[C:3]=1[C:2]([F:1])=[CH:10][CH:9]=3

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 18624498HCID 18624498, compoundHCID 23550270HCID 23550270, compound

Product 1

HCID 69832035HCID 69832035, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [2-[6-fluoro-2-oxo-3-(3,4-dimethyl-1H-pyrrol-2-yl)-1,2-dihydro-benzo[cd]indol-5-ylsulfanyl]-ethyl]-carbamic acid tent-butyl ester (from Example 49 above) (66 mg, 0.145 mmol) in CH2Cl2 (5 mL) was added TFA (Aldrich, 2.5 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour. Aqueous ammonium hydroxide (4 mL) and ethyl acetate were added. The aqueous phase was extracted with ethyl acetate. The ethyl acetate layers were combined and washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by RP-HPLC (C-18, eluted with 1% acetonitrile/0.05% TFA in H2O) to give 5-(2-amino-ethylsulfanyl)-6-fluoro-3-(3,4-dimethyl-1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one trifluoroacetic acid salt as a yellow-green solid. (Yield 20 mg, 29.4%).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by RP-HPLC (C-18, eluted with 1% acetonitrile/0.05% TFA in H2O)

Sources & evidence

ORD record
ord-5a8e45caa9294bdabd9ec32fb170568c
Source dataset
uspto-grants-2003_01
Patent number
US06504034B2

Reaction notes

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