Lithium Hydroxide → HCID 57635973, compound

HRID 2110162Notes

Reaction equation

HRID 2110162 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][C@@H:13]([CH3:15])[N:12]([S:16]([C:19]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:20]=3[CH2:21][CH:22]([C:28]([O:30]C)=[O:29])[CH2:23]4)(=[O:18])=[O:17])[C@@H:11]([CH3:32])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[Li+].[OH-].O1CCCC1.FC(F)(F)C1C=CC(C2CCNCC=2)=CC=1>CO>[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:10][C@@H:11]([CH3:32])[N:12]([S:16]([C:19]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:20]=3[CH2:21][CH:22]([C:28]([OH:30])=[O:29])[CH2:23]4)(=[O:18])=[O:17])[C@@H:13]([CH3:15])[CH2:14]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 12440708Pyridine, 1,2,3,6-tetrahydro-4-[4-(trifluoromethyl)phenyl]-HCID 131727400HCID 131727400, compound

Product 1

HCID 57635973HCID 57635973, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-(4-(3-bromo-4-chlorophenyl)-cis-2,6-dimethylpiperazin-1-ylsulfonyl)-2,3-dihydro-1H-indene-2(R,S)-carboxylate (194 mg, 0.36 mmol), 1N LiOH (2 mL), tetrahydrofuran (8 mL), and methanol (2 mL) was stirred at rt for 2 h. The reaction was poured into 1N HCl (40 mL) and extracted with ethyl acetate (40 mL×2). The combined organic extracts were dried, filtered, and concentrated to give 4-(4-(3-bromo-4-chlorophenyl)-cis-2,6-dimethylpiperazin-1-ylsulfonyl)-2,3-dihydro-1H-indene-2-carboxylic acid: 1H NMR (400 MHz, DMSO-d6): δ 12.30 (br s, 1H), 7.63 (d, 1H), 7.49 (d, 1H), 7.37-7.31 (m, 2H), 7.16 (d, 1H), 6.88 (dd, 1H), 4.04-3.97 (m, 1H), 3.95-3.87 (m, 1H), 3.52-3.44 (m, 2H), 3.40-3.28 (m, 3H), 3.24-3.10 (m, 2H), 2.75-2.64 (m, 2H), 1.35 (d, 6H); MS (ESI): 527.3 (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-033cb4f10738451285d9380dddd1741a
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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