Trifluoroacetic acid → 1-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1-(1,3-dihydroxypropan-2-yl)-1H-indol-5-yl)cyclopropanecarboxamide

HRID 468463Notes

Reaction equation

HRID 468463 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[N:21]([CH:25]([CH2:28][OH:29])[CH2:26][OH:27])[CH:20]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:19]5)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.FC(F)(F)C(O)=O.ClC1C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C1(C)C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[N:21]([CH:25]([CH2:26][OH:27])[CH2:28][OH:29])[C:20]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:19]5)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8371ChloranilHCID 591294261-(Benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1-(1,3-dihydroxypropan-2-yl)indolin-5-yl)cyclopropanecarboxamide

Product 1

HCID 591292921-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1-(1,3-dihydroxypropan-2-yl)-1H-indol-5-yl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(Benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1-(1,3-dihydroxypropan-2-yl)indolin-5-yl)cyclopropanecarboxamide (40.3 mg, 0.0711 mmol as the trifluoracetic acid salt) was dissolved in toluene (1 mL). To the resulting solution was added 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione (35 mg, 0.14 mmol). The resulting suspension was heated at 100 CC in an oil bath for 10 minutes. The crude product was then evaporated to dryness, dissolved in a 1 mL of NA-dimethylformamide and purified by purified by preparative HPLC using a gradient of 0-99% acetonitrile in water containing 0.05% trifluoroacetic acid to yield 1-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-1-(1,3-dihydroxypropan-2-yl)-1H-indol-5-yl)cyclopropanecarbox amide. ESI-MS m/z calc. 450.2, found 451.5 (M+1)+. Retention time of 1.59 minutes.

Workup

  1. temperatureThe resulting suspension was heated at 100 CC in an oil bath for 10 minutes
  2. customThe crude product was then evaporated to dryness
  3. dissolutiondissolved in a 1 mL of NA-dimethylformamide
  4. custompurified
  5. customby purified by preparative HPLC

Sources & evidence

ORD record
ord-91638bed8e7544c7bfc6f8553d670f90
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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