Sodium Hydroxide → 7-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 2389450Notes

Reaction equation

HRID 2389450 reaction equation
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([C:17]3[N:18]([CH3:23])[N:19]=[CH:20][C:21]=3[Br:22])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO>[Br:22][C:21]1[CH:20]=[N:19][N:18]([CH3:23])[C:17]=1[C:15]1[CH:14]=[CH:13][C:9]2[CH:10]([CH3:12])[CH2:11][NH:5][CH2:6][CH2:7][C:8]=2[CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22292801N-Trifluoroacetyl-7-(4-bromo-2-Methyl-2H-pyrazol-3-yl)-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 100645907-(4-Bromo-2-methyl-2H-pyrazol-3-yl)-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepineYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-trifluoroacetyl-7-(4-bromo-2-Methyl-2H-pyrazol-3-yl)-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (37 mg, 0.089 mmol) in methanol (2 mL) was treated with of 15% aqueous NaOH (2 mL), and stirred overnight at 20 C. The product mixture was concentrated, extracted 3 times with CH2Cl2 (5 mL), dried with Na2SO4 and the solvent evaporated. Flash chromatography (0-15% MeOH in CH2Cl2, silica) resulted in 28 mg of a clear oil. 1H NMR (400 MHz, CDCl3) d 7.50 (s, 1H), 7.25 (d, J=8 Hz, 1H), 7.17 (d, J=8 Hz, 1H), 7.10 (s, 1H), 3.83 (s, 3 μl), 3.17 (m, 1H), 3.1-2.9 (m, 8H), 2.80 (dd, J=7, 13 Hz, 1H), 2.48 (bs, 1H), 1.40 (d, J=8 Hz, 3H). MS calculated for C15H18BrN3+H: 320, observed: 320.

Workup

  1. concentrationThe product mixture was concentrated
  2. extractionextracted 3 times with CH2Cl2 (5 mL)
  3. dry with materialdried with Na2SO4
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-2672fb90edfe488db7876826807be54f
Source dataset
uspto-grants-2012_09
Patent number
US08273734B1

Reaction notes

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