Trifluoroacetic acid → HCID 9958978, compound

HRID 2083990Notes

Reaction equation

HRID 2083990 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[C:13]([C:14]([N:16]3[C:24]4[C:19](=[CH:20][C:21]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=5[S:31]([NH2:34])(=[O:33])=[O:32])=[CH:22][CH:23]=4)[CH2:18][CH2:17]3)=[O:15])=[CH:12][C:11]([C:35]([F:38])([F:37])[F:36])=[N:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42]>CO.[Pd]>[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42].[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([N:9]2[C:13]([C:14]([N:16]3[C:24]4[C:19](=[CH:20][C:21]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=5[S:31]([NH2:34])(=[O:32])=[O:33])=[CH:22][CH:23]=4)[CH2:18][CH2:17]3)=[O:15])=[CH:12][C:11]([C:35]([F:36])([F:37])[F:38])=[N:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12043694HCID 12043694, compound

Product 2

HCID 6422Trifluoroacetic acidYield 0.05%HCID 9958978HCID 9958978, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-[[1-[3-Cyanophenyl]-3(trifluoromethyl)-1H-pyrazol-5-yl]carbonyl]-5-[2-(aminosulfonyl)phenyl]-2,3-dihydro-1H-indole (0.2 g, 0.34 mmol), prepared according to Example 4, was reduced under an atmosphere of hydrogen gas (55 psi) in methanol (5 mL) and trifluoroacetic acid in the presence of 10% palladium on carbon catalyst for 18 h at ambient temperature. The reaction mixture was filtered through a pad of Celite® and washed with methanol (3×). This product was treated with trifluoroacetic acid (1 mL) at 80° C. over 1 h, then purified by HPLC utilizing gradient elution with a mixture of water:acetonitrile with 0.05% of trifluoroacetic acid on a reverse phase C18 (60 angstrom) column to give the title product (28 mg, 15%). LRMS (ES+): 598.2 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. washwashed with methanol (3×)
  3. additionThis product was treated with trifluoroacetic acid (1 mL) at 80° C. over 1 h
  4. custompurified by HPLC
  5. washelution
  6. additionwith a mixture of water

Sources & evidence

ORD record
ord-f7b1b35891064cb297cd63b11e4bcb8f
Source dataset
uspto-grants-2004_04
Patent number
US06716841B2

Reaction notes

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