Sodium Hydroxide → HCID 66571488, compound

HRID 534207Notes

Reaction equation

HRID 534207 reaction equation
[CH3:1][S:2]([NH:5][C:6](=[O:37])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][N:21]([C@@H:28]3[CH2:30][C@H:29]3[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)C(=O)C(F)(F)F)[CH2:16][CH2:15]2)=[CH:9][CH:8]=1)(=[O:4])=[O:3].[OH-].[Na+]>CO>[CH3:1][S:2]([NH:5][C:6](=[O:37])[C:7]1[CH:8]=[CH:9][C:10]([CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([CH2:20][NH:21][C@@H:28]3[CH2:30][C@H:29]3[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:18][CH2:19]2)=[CH:11][CH:12]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86708255HCID 86708255, compound

Product 1

HCID 66571488HCID 66571488, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(methylsulfonyl)-4-((4-((2,2,2-trifluoro-N-(trans-2-phenylcyclopropyl)acetamido)methyl)piperidin-1-yl)methyl)benzamide (80 mg, 0.149 mmol) in methanol (2 mL) was added sodium hydroxide (6M, 0.5 mL, 0.500 mmol), and the mixture was stirred at room temperature for 2 h. The mixture was purified using reverse-phase HPLC under the acidic conditions and the fractions containing the product was treated with 1N HCl and concentrated. The residue was dried under vacuum to give 36 mg of product as pale yellow solid. MS: (M+H)+=442.3 1H NMR (400 MHz, DMSO-d6) δ ppm 1.19-1.36 (m, 1H), 1.48-1.72 (m, 3H), 1.91-2.09 (m, 2H), 1.93-2.10 (m, 3H), 2.85-3.26 (m, 5H), 4.30-4.53 (m, 2H), 7.12-7.39 (m, 5H), 7.76 (d, J=8.34 Hz, 2H), 7.71-7.82 (m, 2H), 7.98-8.09 (m, 2H).

Workup

  1. customThe mixture was purified
  2. additionthe fractions containing the product
  3. additionwas treated with 1N HCl
  4. concentrationconcentrated
  5. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-e16ae7b8130f41ecab65e5a34553d5c8
Source dataset
uspto-grants-2014_10
Patent number
US08853408B2

Reaction notes

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