Lithium Hydroxide → HCID 57635982, compound

HRID 2110140Notes

Reaction equation

HRID 2110140 reaction equation
FC(F)(F)OC1C=CC(N2CCNCC2)=CC=1.[CH3:18][O:19][C:20](=[O:51])[CH2:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([S:31]([N:34]3[CH2:39][CH2:38][N:37]([C:40]4[CH:45]=[CH:44][C:43]([O:46][C:47]([F:50])([F:49])[F:48])=[CH:42][CH:41]=4)[CH2:36][CH2:35]3)(=[O:33])=[O:32])[CH:29]=2)[CH:24]=[CH:23]1.[Li+].[OH-].FC(F)(F)C1C=CC(C2CCNCC=2)=CC=1>CO.O1CCCC1>[CH3:18][O:19][C:20](=[O:51])[CH2:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([S:31]([N:34]3[CH2:39][CH2:38][N:37]([C:40]4[CH:41]=[CH:42][C:43]([O:46][C:47]([F:49])([F:50])[F:48])=[CH:44][CH:45]=4)[CH2:36][CH2:35]3)(=[O:33])=[O:32])[CH:29]=2)[CH:24]=[CH:23]1.[F:50][C:47]([F:48])([F:49])[O:46][C:43]1[CH:44]=[CH:45][C:40]([N:37]2[CH2:38][CH2:39][N:34]([S:31]([C:28]3[CH:29]=[C:30]4[C:25]([CH:24]=[CH:23][N:22]4[CH2:21][C:20]([OH:51])=[O:19])=[CH:26][CH:27]=3)(=[O:33])=[O:32])[CH2:35][CH2:36]2)=[CH:41][CH:42]=1

Participants

8

Reactant 4

HCID 3939Lithium HydroxideHCID 12440708Pyridine, 1,2,3,6-tetrahydro-4-[4-(trifluoromethyl)phenyl]-HCID 230811701-(4-(Trifluoromethoxy)phenyl)piperazineHCID 67045834HCID 67045834, compound

Product 2

HCID 57635982HCID 57635982, compoundHCID 67045834HCID 67045834, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

{6-[4-(4-Trifluoromethoxy-phenyl)-piperazine-1-sulfonyl]-indol-1-yl}-acetic acid methyl ester was prepared from 1-(4-trifluoromethoxy-phenyl)-piperazine following the procedures outlined in Example 34. A mixture of {6-[4-(4-trifluoromethoxy-phenyl)-piperazine-1-sulfonyl]-indol-1-yl}-acetic acid methyl ester (45 mg, 0.09 mmol), 1M LiOH (2 mL), tetrahydrofuran (6 mL), and methanol (2 mL) was stirred at rt for 3 h. The reaction was poured into 1M HCl (50 mL) and extracted with ethyl acetate (40 mL×2). The combined organic extracts were dried, filtered, and concentrated to give {6-[4-(4-trifluoromethoxyphenyl)-piperazine-1-sulfonyl]-indol-1-yl}-acetic acid: 1H NMR (400 MHz, DMSO-d6): 67.89 (s, 1H), 7.77 (d, 1H), 7.63 (d, 1H), 7.38 (d, 1H), 7.14 (d, 2H), 6.93 (d, 2H), 6.61 (d, 1H), 5.19 (s, 2H), 3.23-3.15 (m, 4H), 3.03-2.95 (m, 4H); MS (ESI): 483.7 (M+H).

Workup

  1. extractionextracted with ethyl acetate (40 mL×2)
  2. customThe combined organic extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9deed30852b6453bae1c5738f96e8cbf
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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