Sodium Hydroxide → HCID 66571536, compound

HRID 534217Notes

Reaction equation

HRID 534217 reaction equation
FC(F)(F)C([N:5]([CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:38]=[CH:37][C:32]([C:33]([O:35]C)=[O:34])=[CH:31][CH:30]=2)[CH2:24][CH2:23]1)[C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=2)=[CH:11][CH:10]=1)=O.[OH-].[Na+]>CO>[CH3:20][N:18]1[CH:19]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([C@@H:7]3[CH2:8][C@H:6]3[NH:5][CH2:21][CH:22]3[CH2:23][CH2:24][N:25]([CH2:28][C:29]4[CH:30]=[CH:31][C:32]([C:33]([OH:35])=[O:34])=[CH:37][CH:38]=4)[CH2:26][CH2:27]3)=[CH:10][CH:11]=2)[CH:16]=[N:17]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86708264HCID 86708264, compound

Product 1

HCID 66571536HCID 66571536, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-((4-((2,2,2-trifluoro-N-(trans-2-(4-(1-methyl-1H-pyrazol-4-yl)phenyl)cyclopropyl)acetamido)methyl)piperidin-1-yl)methyl)benzoate (67 mg, 0.121 mmol) in methanol (2 mL) was added sodium hydroxide (1M, 0.5 mL, 0.500 mmol), and the mixture was stirred at r room temperature for 18 h. The mixture was purified using reverse-phase HPLC. The fractions containing the product as combined, treated with 1N HCl and concentrated. The residue was dried under vacuum to give 25 mg of product (HCl salt) as white solid. MS: (M+H)+=445.4. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.19-1.37 (m, 1H), 1.51-1.72 (m, 3H), 1.88-2.13 (m, 3H), 2.55-2.65 (m, 1H), 2.85-3.05 (m, 4H), 3.12-3.25 (m, 1H), 3.34 (d, J=11.87 Hz, 2H), 4.34 (d, J=5.05 Hz, 2H), 7.11-7.23 (m, 2H), 7.45-7.55 (m, 2H), 7.71-7.81 (m, 2H), 7.83-7.89 (m, 1H), 7.97-8.06 (m, 2H), 8.10-8.18 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-2c4e45195cfc4f4c8d4eb9551053b92f
Source dataset
uspto-grants-2014_10
Patent number
US08853408B2

Reaction notes

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