Trifluoroacetic acid → HCID 19024426, compound

HRID 1033807Notes

Reaction equation

HRID 1033807 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:23]([N:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27][CH2:26]2)=[O:24])=[CH:17][CH:16]=1)(=[O:8])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>C1(OC)C=CC=CC=1>[CH2:35]([N:22]([CH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:6](=[O:7])(=[O:8])[NH2:5])=[CH:20][CH:19]=1)[C:23]([N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][CH2:26]1)=[O:24])[CH2:36][CH2:37][CH2:38][CH3:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19024457HCID 19024457, compound

Product 1

HCID 19024426HCID 19024426, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

A solution of 86 mg (0.16 mmole) of 1-[N-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]-N-pentylcarbamoyl]-1,2,3,4-tetrahydroquinoline (from Step A), 30 μL of anisole, and 0.8 mL of anhydrous TFA was stirred at room temperature for 16 hours. The residue obtained after evaporation of excess TFA was flash chromatographed over silica gel (elution with 0.5% MeOH in CH2Cl2) to give 55 mg (71%) of the title compound as an off-white foam, homogeneous by TLC (95:5 MeOHCH2Cl2), FAB-MS m/e 492 (M+1)+.

Workup

  1. customThe residue obtained
  2. customafter evaporation of excess TFA
  3. customchromatographed over silica gel (elution with 0.5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-c6e2155533d34335b56f7650457203d9
Source dataset
uspto-grants-1994_05
Patent number
US05312820

Reaction notes

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