Trifluoroacetic acid → HCID 9958978, compound

HRID 2301951Notes

Reaction equation

HRID 2301951 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-af7940c2bb6b4312b64b520ca956ae4f
Source dataset
uspto-grants-2002_08
Patent number
US06429205B1

Reaction notes

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